Updated on 2025/12/04

写真a

 
TOYOTA SHINJI
 
Organization
School of Science Professor
Title
Professor
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News & Topics

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Degree

  • (BLANK) ( The University of Tokyo )

Research Interests

  • Organic Chemistry, Stereochemistry, Aromatic chemistry

  • 有機立体化学

  • 芳香族化学

  • 超分子化学

  • Structual Organic Chemistry

  • 物理有機化学

Research Areas

  • Nanotechnology/Materials / Organic functional materials

  • Nanotechnology/Materials / Functional solid state chemistry

  • Nanotechnology/Materials / Nanometer-scale chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

Research History

  • Institute of Science Tokyo   Professor

    2024.10

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  • Tokyo Institute of Technology   Professor

    2015 - 2024.9

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  • Okayama University of Science   Professor

    2003 - 2015

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  • Okayama University of Science

    1999 - 2003

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  • Okayama University of Science

    1993 - 1998

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  • Okayama University of Science

    1988 - 1993

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Professional Memberships

Papers

  • Expanding Chemistry of Expanded Helicenes Reviewed

    Shinji Toyota

    Chemistry – A European Journal   2025.11

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    Authorship:Lead author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/chem.202502193

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  • Unusually Short H⋅⋅⋅H Contacts in Intramolecularly Cyclized Helically Fused Anthracenes. Reviewed International journal

    Hiroki Fukuda, Eiji Tsurumaki, Kan Wakamatsu, Shinji Toyota

    Chemistry - European Journal   e202401627   2024.5

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    The intramolecular coupling of dichloro-substituted helically fused anthracenes using the Yamamoto coupling yielded cyclized products with sterically congested molecular structures. The X-ray analysis and DFT calculations showed that the aromatic framework adopted a nonplanar structure with a twisted conformation about the newly formed single bond, which acts as a chiral axis. Interestingly, the X-ray structure obtained through the Hirshfeld atom refinement revealed short interatomic distances between the inner hydrogen atoms (1.648-1.692 Å), much shorter than the sum of their van der Waals radii. Owing to these unusually short contacts, the 1H NMR spectrum exhibited a significant deshielding (12.5 ppm) and a large nuclear Overhauser effect (44 %). Additionally, the IR spectrum displayed a high-frequency shift of the C-H stretching vibration. These observations, along with the noncovalent interaction plot indicative of a characteristic steric environment, strongly support the presence of steric hindrance. Moreover, dynamic NMR measurement of the mesityl-substituted derivative yielded a barrier to helical inversion of 84 kJ mol-1. The optical properties and crystal packing of the cyclized products are also reported.

    DOI: 10.1002/chem.202401627

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  • Discovery of internal rotation and conformers of 1,2-dichloroethane: the dawn of the concept of conformation. Invited Reviewed

    Shinji Toyota

    Proceedings of the Japan Academy. Series B, Physical and biological sciences   100 ( 2 )   101 - 113   2024

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    In 1932, Mizushima and Higasi reported the dependence of the dipole moments of 1,2-dichloroethane on both temperature and solvent in the Proceedings of the Imperial Academy, Japan. This report was followed by their first proposal of the existence of conformers that exchanged by internal rotation about a C-C single bond based on experimental data. Their monumental work marked the beginning of the essential concept of conformation in modern stereochemistry. Their proposal was later confirmed by the direct observation of the anti and gauche conformers of 1,2-dichloroethane by Raman spectroscopy, and further supported by other experimental and theoretical methods. The relative stabilities of the anti and gauche conformers of 1,2-dichloroethane and other 1,2-disubstituted ethanes were discussed in terms of steric, electrostatic, and stereoelectronic effects based on analysis of calculated data. Those studies influenced the development of subsequent research in organic chemistry, such as the conformational analysis of cyclohexane derivatives and the isolation of chiral gauche conformers.

    DOI: 10.2183/pjab.100.003

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  • A self-complementary macrocycle by a dual interaction system. Reviewed International journal

    Yuta Sawanaka, Masahiro Yamashina, Hiroyoshi Ohtsu, Shinji Toyota

    Nature communications   13 ( 1 )   5648 - 5648   2022.9

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    Self-complementary assembly is one of the most promising phenomena for the formation of discrete assemblies, e.g., proteins and capsids. However, self-complementary assembly based on multiple host-guest systems has been scarcely reported due to the difficulty in controlling each assembly. Herein, we report a dual interaction system in which the key assembly direction is well regulated by both π-π stacking and hydrogen bonding to construct a self-complementary macrocycle. Continuous host-guest behavior of anthracene-based molecular tweezers during crystallization leads to successful construction of a cyclic hexamer, which is reminiscent of Kekulé's monkey model. Furthermore, the cyclic hexamer in a tight and triple-layered fashion shows hierarchical assembly into cuboctahedron and rhombohedral assemblies in the presence of trifluoroacetic acid. Our findings would be potentially one of metal-free strategies for constructing anthracene-based supramolecular assemblies with higher-order structure.

    DOI: 10.1038/s41467-022-33357-y

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  • Synthesis of Azaylide-Based Amphiphiles by the Staudinger Reaction Reviewed

    Masahiro Yamashina, Hayate Suzuki, Natsuki Kishida, Michito Yoshizawa, Shinji Toyota

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   60 ( 33 )   17915 - 17919   2021.8

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    Authorship:Last author, Corresponding author   Language:English   Publishing type:Research paper (scientific journal)  

    DOI: 10.1002/anie.202105094

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  • Nano-Saturn: Experimental Evidence of Complex Formation of an Anthracene Cyclic Ring with C60 Reviewed

    Yuta Yamamoto, Eiji Tsurumaki, Kan Wakamatsu, Shinji Toyota

    Angewandte Chemie - International Edition   57 ( 27 )   8199 - 8202   2018.7

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    DOI: 10.1002/anie.201804430

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  • Rotational Isomerism Involving Acetylene Carbon Invited Reviewed

    Shinji Toyota

    CHEMICAL REVIEWS   110 ( 9 )   5398 - 5424   2010.9

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    DOI: 10.1021/cr1000628

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  • Alkyne cycloisomerization of 2,7-bis(2-ethynylphenyl)anthracene derivatives to form dinaphtho fused anthracenes Reviewed

    Takumi Morita, Eiji Tsurumaki, Shinji Toyota

    Chemistry Letters   54 ( 9 )   upaf154   2025.9

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    DOI: 10.1093/chemle/upaf154

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  • Substantial Effects of Ring Size on the Structure and Properties of 2,9-Anthrylene Cyclic Oligomers Reviewed

    Yuki Shigihara, Eiji Tsurumaki, Masahiro Yamashina, Shinji Toyota

    Organic Letters   27 ( 31 )   8668 - 8673   2025.8

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    DOI: 10.1021/acs.orglett.5c02610

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  • A Triptycene‐Based Cage Host for Aromatic Hydrocarbon Guests Reviewed

    Takuji Mitani, Yuto Konya, Takehiro Kihara, Eiji Tsurumaki, Shinji Toyota

    Asian Journal of Organic Chemistry   14 ( 6 )   e202500196   2025.6

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    DOI: 10.1002/ajoc.202500196

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  • Synthesis of S-shaped polycyclic aromatic hydrocarbons as anthracene-fused double expanded helicenes by intramolecular alkyne cycloisomerization Reviewed

    Takehiro Kihara, Yu Watanabe, Eiji Tsurumaki, Masahiro Yamashina, Shinji Toyota

    Canadian Journal of Chemistry   2025.5

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    DOI: 10.1139/cjc-2025-0093

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  • Synthesis and Structures of 9,9’‐Bianthryl‐Based Cyclic Dimer and Dinaphtho[c,g]Carbazole via Oxidative Coupling

    Atsuki Shimizu, Shinji Toyota, Tetsuo Iwanaga

    Asian Journal of Organic Chemistry   2025.4

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    DOI: 10.1002/ajoc.202400748

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  • Structures, Chiroptical Properties, and Unexpectedly Facile Helical Inversion of Highly Elongated Anthracene‐Fused Expanded Helicenes

    Hiroki Fukuda, Moe Kobayashi, Eiji Tsurumaki, Masahiro Yamashina, Masashi Hasegawa, Kan Wakamatsu, Shinji Toyota

    Chemistry – A European Journal   2025.2

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    DOI: 10.1002/chem.202404348

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  • Macrocycles composed of biphenylene and butadiyne units with antiaromatic character

    Shoko Nagayama, Hiroki Kawakatsu, Daisuke Asai, Takumi Yokoyama, Masahiro Yamashina, Shinji Toyota, Kazukuni Tahara

    Chemical Science   2025

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    DOI: 10.1039/D5SC04720J

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  • Pseudohelicene chemosensor displaying ternary signaling stimulated by hydrostatic pressure and solvent

    Tomokazu Kinoshita, Kota Watanabe, Eiji Tsurumaki, Shinji Toyota, Gaku Fukuhara

    Chemical Communications   2025

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    DOI: 10.1039/D4CC05652C

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  • Solid-State Self-Assembly: Exclusive Formation and Dynamic Interconversion of Discrete Cyclic Assemblies Based on Molecular Tweezers. International journal

    Koki Okabe, Masahiro Yamashina, Eiji Tsurumaki, Hidehiro Uekusa, Shinji Toyota

    The Journal of organic chemistry   89 ( 13 )   9488 - 9495   2024.7

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    In contrast to self-assembly in solution systems, the construction of well-defined assemblies in the solid state has long been identified as a challenging task. Herein, we report the formation of tweezers-shaped molecules into various assemblies through a solid-state self-assembly strategy. The relatively flexible molecular tweezers undergo exclusive and quantitative assembly into either cyclic hexamers or a porous network through classical recrystallization or the exposure of powders to solvent vapor, despite the fact that they form only dimers in solution. The cyclic hexamers have high thermal stability and exhibit moderate solid-state fluorescence. The formation of heterologous assemblies consisting of different tweezers allows for tuning these solid-state properties of the cyclic hexamer. Furthermore, (trimethylsilyl)ethynyl-substituted tweezers demonstrate solvent-vapor-induced dynamic interconversion between the cyclic hexamer and a pseudocyclic dimer in the solid state. This assembly behavior, which has been studied extensively in solution-based supramolecular chemistry, had not been accomplished in the solid state so far.

    DOI: 10.1021/acs.joc.4c00794

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  • Structure and Chiroptical Properties of Anthra[1,2-a]anthracene-1-yl Dimers as New Biaryls. International journal

    Kota Watanabe, Eiji Tsurumaki, Masashi Hasegawa, Shinji Toyota

    Chemistry (Weinheim an der Bergstrasse, Germany)   30 ( 31 )   e202400929   2024.6

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    Dimers of anthra[1,2-a]anthracene-1-yl units and its mesityl derivative were synthesized by Ni(0)-mediated coupling of the corresponding chloro derivatives as new biaryls. The X-ray analysis and DFT calculations revealed that two polycyclic aromatic units with nonplanar deformations took a twisted conformation about the single bond as a chiral axis. Enantiomers of the nonsubstituted compound were resolved by chiral HPLC, and the enantiopure samples showed intense Cotton effects at 321 nm in the circular dichroism (CD) spectra and emission bands at 449 nm in the circularly polarized luminescence (CPL) spectra with dissymmetry factor of |glum| 3.6×10-3. The absolute stereochemistry of this biaryl was determined by the theoretical calculation of CD spectrum by the time-dependent DFT method. The barrier to enantiomerization was determined to be 108 kJ mol-1 at 298 K. The dynamic process proceeded via a stepwise mechanism involving the helical inversion of each aromatic unit and the rotation about the biaryl axis as analyzed by the DFT calculations.

    DOI: 10.1002/chem.202400929

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  • Azaylide-based gemini amphiphiles displaying unique self-assembling behavior via an even–odd effect of alkyl linker chain length

    Yoshimori Akiyama, Masahiro Yamashina, Shinji Toyota

    Soft Matter   2024

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    DOI: 10.1039/D4SM00789A

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  • Transformation of Highly Hydrophobic Triarylphosphines into Amphiphiles via Staudinger Reaction with Hydrophilic Trichlorophenyl Azide. International journal

    Hayate Suzuki, Yoshimori Akiyama, Masahiro Yamashina, Yuya Tanaka, Shinji Toyota

    Chemistry (Weinheim an der Bergstrasse, Germany)   29 ( 72 )   e202303017   2023.12

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    Owing to its hydrophobic properties and reactivity, triarylphosphines (PAr3 ) are promising precursors for the development of new amphiphiles. However, an efficient and reliable synthetic method for amphiphiles based on highly hydrophobic PAr3 is still required. Herein, a straightforward transformation of highly hydrophobic PAr3 into amphiphiles via the Staudinger reaction is reported. By simply mixing PAr3 and a hydrophilic trichlorophenyl azide containing two hydrophilic chains, amphiphiles bearing a N=P bond (i. e., an azaylide moiety) were quantitatively formed. The obtained azaylide-based amphiphiles were remarkably water-soluble, enabling their spontaneous self-assembly into 2 nm-sized micelles composed of 4-5 molecules in water with a low critical micelle concentration (up to 0.05 mM or less) due to the effective intermolecular interactions among the hydrophobic surfaces. Although the azaylide moiety is easily hydrolyzed in the presence of water, the azaylide in the amphiphiles displayed notable stability in water even at 60 h, which stems from the LUMO modulation induced by the presence of three electron-withdrawing chloro groups and two twisted alkoxycarbonyl groups, according to DFT calculations. An amphiphile having a large hydrophobic surface solubilized various hydrophobic organic dyes through efficient intermolecular interactions, resulting in the dyes exhibiting either monomer or excimer emissions in water.

    DOI: 10.1002/chem.202303017

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  • Controlling the Assembly of PdII/Bianthryl‐Based Monomeric and Dimeric Interlocked Cages by Steric Effects

    Sota Watanabe, Masahiro Yamashina, Eiji Tsurumaki, Shinji Toyota

    ChemistryEurope   2023.11

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    DOI: 10.1002/ceur.202300047

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  • Synthesis and Properties of Rubicene-Based Aromatic π-Conjugated Compounds as Five-Membered Ring Embedded Planar Nanographenes. Reviewed International journal

    Shinji Toyota, Sayaka Ban, Muneyasu Hara, Masahiko Kawamura, Hiroshi Ikeda, Eiji Tsurumaki

    Chemistry (Weinheim an der Bergstrasse, Germany)   29 ( 49 )   e202301346   2023.9

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    Polycyclic aromatic hydrocarbons consisting of two or three rubicene substructures were designed as π-conjugated compounds embedding five-membered rings. The target compounds with t-butyl groups were synthesized by the Scholl reaction of precursors consisting of 9,10-diphenylanthracene units, even though a partially precyclized precursor was required for the synthesis of the trimer. These compounds were isolated as stable and dark blue solids. Single-crystal X-ray analysis and DFT calculations revealed the planar aromatic framework of these compounds. In the electronic spectra, the absorption and emission bands were considerably red-shifted compared with those of the reference rubicene compound. In particular, the emission band of the trimer extended to the near-IR region while retaining the emissive property. The narrowed HOMO-LUMO gap with the extension of the π-conjugation was confirmed by cyclic voltammetry and DFT calculations.

    DOI: 10.1002/chem.202301346

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  • Synthesis and Photophysical Properties of Anthracene Bisimide–butadiynylene Linear Dimer and Trimer Reviewed

    Tetsuo Iwanaga, Keisuke Tanaka, Kento Kawano, Natsuki Yamashita, Tenta Ishikawa, Shinji Toyota

    Chemistry Letters   52 ( 4 )   233 - 236   2023.4

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    Authorship:Last author   Publishing type:Research paper (scientific journal)   Publisher:The Chemical Society of Japan  

    DOI: 10.1246/cl.230012

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  • Structures and Supramolecular Properties of Inclusion Complexes of Anthracene-Triptycene Nanocages with Fullerene Guests and Their Dynamic Motion as Molecular Gyroscopes. Reviewed International journal

    Takuji Mitani, Eiji Tsurumaki, Shinji Toyota

    Chemistry - European Journal   29 ( 12 )   e202203462   2023.2

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    Three derivatives of macrocyclic cage compounds consisting of diarylanthracene and triptycene units were synthesized. These nanocages formed host-guest complexes with C60 and other fullerene guests as confirmed by 1 H NMR and fluorescence spectroscopy. The association constant of the mesityl and 2,4,6-tributoxyphenyl derivatives with C60 was determined to be 2.2 × 104  L mol-1 , which was larger than that of the pentafluorophenyl derivative. Direct experimental evidence of the complexation was obtained by X-ray diffraction analysis: the guest C60 molecule was included in the cavity via multipoint CH⋅⋅⋅π interactions. Dynamic disorders of the included C60 molecule in variable-temperature X-ray analysis indicated uniaxial motion, such as gyroscopic motion. The unique dynamic behavior of the spherical C60 rotor anchored by the cage stator via CH⋅⋅⋅π interactions in the crystal, as well as substituent effects on the association properties, are discussed with the aid of DFT calculations.

    DOI: 10.1002/chem.202203462

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  • Substituent effects on helical structures and chiroptical properties of fused anthracenes with bulky phenyl groups Reviewed

    Kenta Suzuki, Hiroki Fukuda, Hayato Toda, Yoshitane Imai, Yuki Nojima, Masashi Hasegawa, Eiji Tsurumaki, Shinji Toyota

    Tetrahedron   132   133243 - 133243   2023.2

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    DOI: 10.1016/j.tet.2022.133243

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  • Synthesis, Structures, and Complexation with Phenolic Guests of Acridone-Incorporated Arylene-Ethynylene Macrocyclic Compounds. Reviewed International journal

    Takashi Komori, Eiji Tsurumaki, Shinji Toyota

    Chemistry, an Asian journal   18 ( 1 )   e202201003   2023.1

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    Acridone units were incorporated into the arylene-ethynylene structure as polar arene units. Cyclic trimers consisting of three acridone-2,7-diyl units and three 1,3-phenylene units were synthesized by Sonogashira couplings via stepwise or direct route. X-ray analysis revealed that the trimer had a nearly planar macrocyclic framework with a cavity surrounded by three carbonyl groups. In contrast, the corresponding tetramer had a nonplanar macrocyclic framework. 1 H NMR measurements showed that the trimer formed a 1 : 1 complex as a macrocyclic host with dihydric phenol guests, and the association constants were determined to be ca. 1.0×103  L mol-1 for hydroquinone or resorcinol guests in CDCl3 at 298 K. The calculated structures of these complexes by the DFT method supported the presence of two sets of OH⋅⋅⋅O=C hydrogen bonds between the host and guest molecules. The spectroscopic data of the cyclic trimers and tetramers are compared with those of reference acridone compounds.

    DOI: 10.1002/asia.202201003

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  • Iterative synthesis, structures, and properties of acyclic and cyclic acridone oligomers

    Takashi Komori, Eiji Tsurumaki, Shinji Toyota

    Asian Journal of Organic Chemistry   2022.11

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    DOI: 10.1002/ajoc.202200508

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  • An Alternative Synthesis of Tribenzodecacyclenes and Experimental Barrier to Propeller Inversion Reviewed

    Shun Fukamizo, Hiroshi Ikeda, Eiji Tsurumaki, Shinji Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   95 ( 4 )   652 - 656   2022.4

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    DOI: 10.1246/bcsj.20220015

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  • A pressure-induced ratiometric signalling chemosensor: a case of helical anthracenes. Reviewed International journal

    Tomokazu Kinoshita, Kei Fujise, Eiji Tsurumaki, Shinji Toyota, Gaku Fukuhara

    Chemical communications (Cambridge, England)   58 ( 20 )   3290 - 3293   2022.3

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    Language:English   Publishing type:Research paper (scientific journal)   Publisher:Royal Society of Chemistry ({RSC})  

    One of the helical anthracenes, [4]HA, in which two fused anthracene ends are spatially arranged top and bottom, exhibits a ratiometric fluorescence response due to the hydrostatic pressure-dependent intramolecular [4+4] photocyclodimerization. This ratiometric signalling comes from the formation of an intramolecular stacked species and its subsequent photoreaction upon hydrostatic pressurization. The ratiometric indexes as a function of hydrostatic pressure may enable us to quantify an unknown pressure in solutions.

    DOI: 10.1039/d2cc00428c

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  • Synthesis, Structures, and Properties of Helically Fused Anthraquinones with Unusually Close Carbonyl-Carbonyl Contacts. Reviewed International journal

    Kozue Morioka, Kan Wakamatsu, Eiji Tsurumaki, Shinji Toyota

    Chemistry - Europeana Jounral (Weinheim an der Bergstrasse, Germany)   28 ( 1 )   e202103694   2022.1

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    Electron-deficient aromatic ketones consisting of three fused anthraquinone units were synthesized by oxidation of the corresponding fused anthracenes. X-ray analysis revealed that these compounds had nonplanar helical structures with unusual contacts, C=O⋅⋅⋅C=O 2.467 Å, between the inner carbonyl groups. The role of n⋅⋅⋅π* interactions in the short contacts was evaluated using a noncovalent interaction plot and natural bond orbital analysis. The dynamic process involving helical inversion was observed by the variable temperature 1 H NMR measurement of a derivative with 2,4,6-trimethylphenyl groups, and the barrier was estimated to be 77 kJ mol-1 . DFT calculations indicated that the helical inversion proceeded via a multistep mechanism. The characteristic spectroscopic and electrochemical data due to the electron-deficient anthraquinone units and the sterically congested carbonyl groups are discussed with the aid of DFT calculations.

    DOI: 10.1002/chem.202103694

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  • Structure and Photophysical Properties of 1,1,2,2-Tetra(1-anthryl)ethane: A C(sp3 )-C(sp3 ) Bond Substituted with Four Anthracene Units. Reviewed International journal

    Shu Aoki, Eiji Tsurumaki, Masahiro Yamashina, Kan Wakamatsu, Shinji Toyota

    ChemPlusChem   87 ( 1 )   e202100447   2022.1

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    The title aromatic compound comprising four anthracene units was synthesized by the McMurry coupling of di(1-anthryl) ketone as a hydrogenated product in 65 % yield. The molecule forms a C2 symmetric structure with the ap conformation about the C(sp3 )-C(sp3 ) single bond, as revealed by X-ray analysis and DFT calculations. The UV/vis and fluorescence spectra of this compound were compared with those of anthracene, di(1-anthryl)methane, and 1,2-di(1-anthryl)ethane. The fluorescence spectrum showed a broad emission band at 450 nm having a long lifetime at 21 ns, which was assignable to an excimer-type emission, in contrast to the other reference compounds. The characteristic photophysical property is discussed in terms of the molecular structure with the aid of the noncovalent interaction plots and the conformational analysis.

    DOI: 10.1002/cplu.202100447

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  • Synthesis, Structures, and Electronic Properties of 2,7-Anthrylene-Based Azacyclophanes Bearing o-, m-, and p-Phenylenediamine Linkers Reviewed

    Tetsuo Iwanaga, Takashi Komori, Hiroki Sato, Shuichi Suzuki, Tomokazu Yamauchi, Yohji Misaki, Hiroyasu Sato, Shinji Toyota

    The Journal of Organic Chemistry   86 ( 17 )   11370 - 11377   2021.9

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    Publishing type:Research paper (scientific journal)   Publisher:American Chemical Society (ACS)  

    DOI: 10.1021/acs.joc.1c00856

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  • Synthesis of Azaylide‐Based Amphiphiles by the Staudinger Reaction

    Masahiro Yamashina, Hayate Suzuki, Natsuki Kishida, Michito Yoshizawa, Shinji Toyota

    Angewandte Chemie   133 ( 33 )   18059 - 18063   2021.8

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/ange.202105094

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  • Cyclic monoterpenes trapped in a polyaromatic capsule: unusual selectivity, isomerization, and volatility suppression Reviewed

    Ryuki Sumida, Yuya Tanaka, Keita Niki, Yoshihisa Sei, Shinji Toyota, Michito Yoshizawa

    CHEMICAL SCIENCE   12 ( 29 )   9946 - 9951   2021.8

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    DOI: 10.1039/d1sc01987b

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  • Complexation of an Anthracene-Triptycene Nanocage Host with Fullerene Guests through CH⋅⋅⋅π Contacts. Reviewed International journal

    Kazuki Kajiyama, Eiji Tsurumaki, Kan Wakamatsu, Gaku Fukuhara, Shinji Toyota

    ChemPlusChem   86 ( 5 )   716 - 722   2021.5

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    A bicyclic anthracene macrocycle containing two triptycene units at the bridgehead positions was synthesized by Ni-mediated coupling of the corresponding precursor as a cage-shaped aromatic hydrocarbon host. This cage host formed an inclusion complex with C60 or C70 guest in 1 : 1 ratio in solution. The association constants (Ka ) determined by the fluorescence titration method were 1.3×104 and 3.3×105  L mol -1 for the C60 and C70 complexes, respectively, at 298 K in toluene. DFT calculations revealed that the guest molecules were included in the middle of the cavity with several CH⋅⋅⋅π contacts. The strong affinity of the cage host for the fullerene guests and the high selectivity toward C70 are discussed on the basis of spectroscopic and structural data.

    DOI: 10.1002/cplu.202000816

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  • Front Cover: Construction of Helical Structures with Multiple Fused Anthracenes: Structures and Properties of Long Expanded Helicenes (Chem. Eur. J. 14/2021)

    Kei Fujise, Eiji Tsurumaki, Kan Wakamatsu, Shinji Toyota

    Chemistry – A European Journal   27 ( 14 )   4473 - 4473   2021.3

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    Publishing type:Research paper (scientific journal)   Publisher:Wiley  

    DOI: 10.1002/chem.202005357

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  • Construction of Helical Structures with Multiple Fused Anthracenes: Structures and Properties of Long Expanded Helicenes. Reviewed International journal

    Kei Fujise, Eiji Tsurumaki, Kan Wakamatsu, Shinji Toyota

    Chemistry - European Jounral (Weinheim an der Bergstrasse, Germany)   27 ( 14 )   4548 - 4552   2021.3

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    Polycyclic aromatic compounds consisting of four or five fused anthracene units were synthesized by PtCl2 -catalyzed cycloisomerization as novel long expanded helicenes. These compounds have helical structures with significant stacking of the terminal anthracene moieties at 0.33 nm interlayer distance. In the UV-vis and fluorescence spectra, the absorption and emission bands were red-shifted as the number of fused anthracene units was increased. The characteristic broad and long-lived emission bands of the long analogues are explained by the excimer-like stabilization of the excited state. These photophysical data as well as their cyclic voltammetric data are discussed on the basis of the π-conjugation and interlayer π⋅⋅⋅π interactions in the molecular structures and the molecular orbitals. The barrier and mechanism of helical inversion are also reported.

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  • Multiple Fused Anthracenes as Helical Polycyclic Aromatic Hydrocarbon Motif for Chiroptical Performance Enhancement Reviewed

    Kei Fujise, Eiji Tsurumaki, Gaku Fukuhara, Nobuyuki Hara, Yoshitane Imai, Shinji Toyota

    CHEMISTRY-AN ASIAN JOURNAL   15 ( 16 )   2456 - 2461   2020.8

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    DOI: 10.1002/asia.202000394

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  • Construction of Anthracene Bisimide-based Donor–Acceptor–Donor Arrays with 6,13-Diethynylpentacenes and 9,10-Diethynylanthracenes as Extended π-Conjugated Systems Reviewed

    Johannes Nebauer, Tenta Ishikawa, Shinji Toyota, Rik R. Tykwinski, Tetsuo Iwanaga

    Chemistry Letters   49 ( 7 )   781 - 784   2020.7

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    DOI: 10.1246/cl.200234

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  • Theoretical Studies of Structures and Conformational Analysis of Anthracene-2,7-diyl Cyclic Oligomers Reviewed

    Shinji Toyota, Kan Wakamatsu

    Bulletin of the Chemical Society of Japan   2019.11

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    DOI: 10.1246/bcsj.20190280

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  • Nano-Saturn with an Ellipsoidal Body: Anthracene Macrocyclic Ring-C70 Complex Reviewed

    Shinji Toyota, Yuta Yamamoto, Kan Wakamatsu, Eiji Tsurumaki, Alvaro Munoz-Castro

    Bulletin of the Chemical Society of Japan   92 ( 10 )   1721 - 1728   2019.10

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    DOI: 10.1246/bcsj.20190133

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  • Quadruple and Sextuple Triptycene Gears in Macrocyclic Frameworks Reviewed

    Shinji Toyota, Kenta Kawahata, Kota Sugahara, Tomohiro Oki, Tetsuo Iwanaga

    Asian Journal of Organic Chemistry   8 ( 10 )   1919 - 1923   2019.10

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    DOI: 10.1002/ajoc.201900421

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  • Chemistry of Anthracene−Acetylene Oligomers XXVII. Iterative Synthesis, Structures, and Properties of Anthracene−Diacetylene Cyclic Oligomers with 10‐Mesitylanthracene‐1,8‐diyl Units Reviewed

    Shinji Toyota, Manami Yoshikawa, Toyoaki Saibara, Yuya Yokoyama, Takashi Komori, Tetsuo Iwanaga

    ChemPlusChem   84 ( 6 )   643 - 654   2019.6

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    DOI: 10.1002/cplu.201800433

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  • Novel Aromatics: Official Special Issue of ISNA‐18 Reviewed

    Aiko Fukazawa, Shinji Toyota, Rik Tykwinski, Wallace Wong

    ChemPlusChem   84 ( 6 )   562   2019.6

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    DOI: 10.1002/cplu.201900232

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  • Exploration of Nano‐Saturns: A Spectacular Sphere–Ring Supramolecular System Reviewed

    Shinji Toyota, Eiji Tsurumaki

    Chemistry – A European Journal   25 ( 28 )   6878 - 6890   2019.5

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    DOI: 10.1002/chem.201900039

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  • Synthesis and photophysical properties of dinaphtho[2,3-b:2 ',3 '-i] dihydrophenazine derivatives Reviewed

    Iwanaga Tetsuo, Asano Naoto, Yamada Haruo, Toyota Shinji

    TETRAHEDRON LETTERS   60 ( 16 )   1113 - 1116   2019.4

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  • Box-shaped cyclic oligoarenes: Synthesis and Structure of Anthracene-1,8-diyl Cyclic Tetramers Reviewed

    K. Fujise, T. Saibara, T. Iwanaga, E. Tsurumaki, S. Toyota

    Chem. Lett.   48 ( 2 )   166 - 169   2019.2

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  • Inclusion of chlorinated hydrocarbon guests by 9,9'-bianthracene host and its selectivity Reviewed

    Toyota Shinji, Yokoyama Aya, Tanaka Kunihiko, Akaki Yusuke, Iwanaga Tetsuo

    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY   92 ( 1-2 )   129 - 136   2018.10

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  • Synthesis and Conformational Analysis of 10-Mesitylanthracene-1,8-diyl Oligomers Reviewed

    Toyota Shinji, Saibara Toyoaki, Fujise Kei, Oki Tomohiro, Iwanaga Tetsuo

    SYNLETT   29 ( 16 )   2137 - 2140   2018.10

  • Donor-Donor'-Acceptor Triads Based on [3.3]Paracyclophane with a 1,4-Dithiafulvene Donor and a Cyanomethylene Acceptor: Synthesis, Structure, and Electrochemical and Photophysical Properties Reviewed

    Sako Katsuya, Hasegawa Tomoya, Onda Hiroyuki, Shiotsuka Michito, Watanabe Motonori, Shinmyozu Teruo, Tojo Sachiko, Fujitsuka Mamoru, Majima Tetsuro, Hirao Yasukazu, Kubo Takashi, Iwanaga Tetsuo, Toyota Shinji, Takemura Hiroyuki

    CHEMISTRY-A EUROPEAN JOURNAL   24 ( 44 )   11407 - 11416   2018.8

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    DOI: 10.1002/chem.201801774

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  • Synthesis and Electronic Properties of Length-Defined 9,10-Anthrylene-Butadiynylene Oligomers Reviewed

    Maiko Nagaoka, Eiji Tsurumaki, Mai Nishiuchi, Tetsuo Iwanaga, Shinji Toyota

    Journal of Organic Chemistry   83 ( 10 )   5784 - 5790   2018.5

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    DOI: 10.1021/acs.joc.8b00311

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  • Experimental and theoretical studies on thermodynamics and properties of tautomers of 2-substituted 6(4)-methyl-1,4(1,6)-dihydropyrimidine-5-carboxylates Reviewed

    Hidetsura Cho, Yoshio Nishimura, Hiroshi Ikeda, Mitsuhiro Asakura, Shinji Toyota

    Tetrahedron   74 ( 20 )   2405 - 2413   2018.5

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    DOI: 10.1016/j.tet.2018.03.032

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  • Facile Synthesis of Rubicenes by Scholl Reaction Reviewed

    Masahiko Kawamura, Eiji Tsurumaki, Shinji Toyota

    Synthesis (Germany)   50 ( 1 )   134 - 138   2018.1

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    DOI: 10.1055/s-0036-1588570

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  • Structures and Photophysical Properties of a 1,8-Anthrylene-Ethenylene Cyclic Tetramer Reviewed

    Masataka Inoue, Takashi Komori, Tetsuo Iwanaga, Shinji Toyota

    CHEMISTRY LETTERS   46 ( 12 )   1836 - 1838   2017.12

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    DOI: 10.1246/cl.170884

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  • Oxidation State-Dependent Intramolecular Electronic Interaction of Carbazole-Based Azacyclophanes with 9,10-Anthrylene Units Reviewed

    Tetsuo Iwanaga, Tomokazu Yamauchi, Shinji Toyota, Shuichi Suzuki, Keiji Okada

    JOURNAL OF ORGANIC CHEMISTRY   82 ( 19 )   10699 - 10703   2017.10

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    DOI: 10.1021/acs.joc.7b01688

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  • Triple and Quadruple Triptycene Gears in Rigid Macrocyclic Frameworks Reviewed

    Shinji Toyota, Kenta Kawahata, Kota Sugahara, Kan Wakamatsu, Tetsuo Iwanaga

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 37 )   5696 - 5707   2017.10

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    DOI: 10.1002/ejoc.201701067

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  • Planar Anthracene-Acetylene Frameworks as a Stereogenic Motif Reviewed

    Shinji Toyota, Hiroshi Ikeda, Tetsuo Iwanaga

    CHEMPLUSCHEM   82 ( 7 )   957 - 966   2017.7

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  • Synthesis of 1,8-Anthracene-Ethenylene Cyclic Dimers and Related Compounds: Effects of Linkers on their Structures, Electronic Properties, and Dynamic Behavior Reviewed

    Masataka Inoue, Tetsuo Iwanaga, Shinji Toyota

    ASIAN JOURNAL OF ORGANIC CHEMISTRY   6 ( 5 )   566 - 574   2017.5

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    DOI: 10.1002/ajoc.201700046

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  • Synthesis, structures, and properties of 2,5-dianthrylthiophene derivatives Reviewed

    Shinji Toyota, Mai Nishiuchi, Taisei Iwata, Tomokazu Yamauchi, Tetsuo Iwanaga, Masashi Hasegawa

    CANADIAN JOURNAL OF CHEMISTRY   95 ( 3 )   286 - 291   2017.3

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    DOI: 10.1139/cjc-2016-0391

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  • Macrocyclic 2,7-Anthrylene Oligomers Reviewed

    Yuta Yamamoto, Kan Wakamatsu, Tetsuo Iwanaga, Hiroyasu Sato, Shinji Toyota

    CHEMISTRY-AN ASIAN JOURNAL   11 ( 9 )   1370 - 1375   2016.5

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    DOI: 10.1002/asia.201600230

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  • Intramolecular Charge-Transfer Interaction of Donor-Acceptor-Donor Arrays Based on Anthracene Bisimide Reviewed

    Tetsuo Iwanaga, Marina Ogawa, Tomokazu Yamauchi, Shinji Toyota

    JOURNAL OF ORGANIC CHEMISTRY   81 ( 10 )   4076 - 4080   2016.5

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    DOI: 10.1021/acs.joc.6b00364

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  • Efficient Synthesis and Electronic Spectra of Unsymmetrical 5,12-Diethynyltetracene Derivatives Reviewed

    Tetsuo Iwanaga, Yuta Yamamoto, Keita Nishioka, Shinji Toyota

    SYNTHESIS-STUTTGART   47 ( 24 )   3997 - 4007   2015.12

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    DOI: 10.1055/s-0035-1560474

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  • An Enantiopure 5,5-Bitetracene Reviewed

    Shinji Toyota, Ryutaro Miyaji, Yuta Yamamoto, Masataka Inoue, Kan Wakamatsu, Tetsuo Iwanaga

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 35 )   7648 - 7651   2015.12

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    DOI: 10.1002/ejoc.201501135

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  • Structures, Dynamic Behavior, and Spectroscopic Properties of 1,8-Anthrylene-Ethenylene Cyclic Dimers and Their Substituent Effects Reviewed

    Masataka Inoue, Tetsuo Iwanaga, Shinji Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   88 ( 11 )   1591 - 1602   2015.11

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    DOI: 10.1246/bcsj.20150245

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  • Cramping an Alkyl Group by Rigid Macrocyclic Framework Reviewed

    Shinji Toyota, Tomohiro Oki, Masataka Inoue, Kan Wakamatsu, Tetsuo Iwanaga

    CHEMISTRY LETTERS   44 ( 7 )   978 - 980   2015.7

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    DOI: 10.1246/cl.150340

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  • Effective Synthesis of Ethynylanthracene Derivatives and Their Applications to Oligomer Synthesis Reviewed

    Shinji Toyota, Tetsuo Iwanaga

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN   73 ( 4 )   328 - 338   2015.4

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    DOI: 10.5059/yukigoseikyokaishi.73.328

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  • Yuki Gosei Kagaku Kyokaishi Reviewed

    S. Toyota, T. Iwanaga

    Yuki Gosei Kagaku Kyokaishi   73 ( 4 )   328 - 338   2015.4

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  • Chemistry of Anthracene-Acetylene Oligorners XXV: On-Surface Chirality of a Self-Assembled Molecular Network of a Fan-Blade-Shaped Anthracene-Acetylene Macrocycle with a Long Alkyl Chain Reviewed

    Takuya Tsuya, Kohei Iritani, Kazukuni Tahara, Yoshito Tobe, Tetsuo Iwanaga, Shinji Toyota

    CHEMISTRY-A EUROPEAN JOURNAL   21 ( 14 )   5520 - 5527   2015.3

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    DOI: 10.1002/chem.201405638

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  • Chemistry of Anthracene Acetylene Oligomers. XXIV. Theoretical Evaluation of Molecular Strain and Interactions in Anthracene Acetylene Cyclic Oligomers by Homodesmotic Reaction Method Reviewed

    Shinji Toyota, Kan Wakamatsu, Takahiro Kawakami, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   88 ( 2 )   283 - 291   2015.2

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    DOI: 10.1246/bcsj.20140294

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  • Synthesis and Properties of Extended pi-Conjugated Compounds with 9,10-Bis(phenylethynyl)anthracene Units Reviewed

    Shinji Toyota, Sayaka Karashima, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   88 ( 1 )   192 - 199   2015.1

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    DOI: 10.1246/bcsj.20140279

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  • Synthesis of 2,9-Diethynylanthracene Derivatives Reviewed

    Shinji Toyota, Takahiro Kawakami, Tetsuo Iwanaga

    SYNTHESIS-STUTTGART   46 ( 12 )   1667 - 1673   2014.6

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    DOI: 10.1055/s-0033-1338608

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  • Introduction of an Arylethynyl Group onto an Anthracene Bisimide Core for Molecular Design of New pi-Conjugated Compounds Reviewed

    Tetsuo Iwanaga, Ryo Tanaka, Shinji Toyota

    CHEMISTRY LETTERS   43 ( 1 )   105 - 107   2014.1

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    DOI: 10.1246/cl.130842

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  • Synthesis and properties of novel crown ether-annelated 4 ',5 '-diaza-9 '-(1,3-dithiole-2-ylidene)-fluorenes and their ruthenium(II) complexes Reviewed

    Katsuya Sako, Toshiaki Kakehi, Shota Nakano, Hiroyuki Oku, Xu Feng Shen, Tetsuo Iwanaga, Manami Yoshikawa, Kouta Sugahara, Shinji Toyota, Hiroyuki Takemura, Teruo Shinmyozu, Michito Shiotsuka, Hitoshi Tatemitsu

    TETRAHEDRON LETTERS   55 ( 3 )   749 - 752   2014.1

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    DOI: 10.1016/j.tetlet.2013.12.013

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  • Three-Dimensional Aromatic Networks Reviewed

    Shinji Toyota, Tetsuo Iwanaga

    POLYARENES II   350   111 - 140   2014

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    DOI: 10.1007/128_2012_358

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  • Chemistry of Anthracene Acetylene-Oligomers. XXIII. Molecular Structures and Stereochemistry of Anthracene-Diacetylene Cyclic Dimers Having Two Intraannular Alkoxy Groups Reviewed

    Shinji Toyota, Takuya Tsuya, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   86 ( 11 )   1309 - 1316   2013.11

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    DOI: 10.1246/bcsj.20130186

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  • Strained and Fluxional Macrocyclic Framework of Anthracene-Diacetylene Cyclic Pentamers Reviewed

    Manami Yoshikawa, Sakiko Imigi, Kan Wakamatsu, Tetsuo Iwanaga, Shinji Toyota

    CHEMISTRY LETTERS   42 ( 5 )   559 - 561   2013.5

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    DOI: 10.1246/cl.130100

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  • Efficient Synthesis of 9,10-Bis(phenylethynyl)anthracene Derivatives by Integration of Sonogashira Coupling and Double-Elimination Reactions Reviewed

    Shinji Toyota, Daiki Mamiya, Rie Yoshida, Ryo Tanaka, Tetsuo Iwanaga, Akihiro Orita, Junzo Otera

    SYNTHESIS-STUTTGART   45 ( 8 )   1060 - 1068   2013.4

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    DOI: 10.1055/s-0032-1316867

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  • Chemistry of Anthracene-Acetylene Oligomers. XXI. Structures and Stereochemistry of Chiral Anthracene-Acetylene Dimers with an Intra-Annular Alkoxy Group Reviewed

    Takuya Tsuya, Tetsuo Iwanaga, Shinji Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   86 ( 1 )   138 - 145   2013.1

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    DOI: 10.1246/bcsj.20120251

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  • Nonplanar and dynamic structures of 1,8-Anthrylene-Ethenylene cyclic dimers Reviewed

    Masataka Inoue, Tetsuo Iwanaga, Shinji Toyota

    Chemistry Letters   42 ( 12 )   1499 - 1501   2013

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    DOI: 10.1246/cl.130765

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  • Tolanophane Revisited - Resolution and Racemization Mechanism of a Twisted Chiral Aromatic Compound Reviewed

    Shinji Toyota, Katsutoshi Kawai, Tetsuo Iwanaga, Kan Wakamatsu

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   ( 29 )   5679 - 5684   2012.10

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    DOI: 10.1002/ejoc.201200765

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  • Chemistry of Anthracene-Acetylene Oligomers XX: Synthesis, Structures, and Self-Association of Anthracene-Anthraquinone Cyclic Compounds with Ethynylene Linkers Reviewed

    Tetsuo Iwanaga, Kazuaki Miyamoto, Kazukuni Tahara, Koji Inukai, Satoshi Okuhata, Yoshito Tobe, Shinji Toyota

    CHEMISTRY-AN ASIAN JOURNAL   7 ( 5 )   935 - 943   2012.5

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    DOI: 10.1002/asia.201101000

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  • Trimethylsumanene: Enantioselective Synthesis, Substituent Effect on Bowl Structure, Inversion Energy, and Electron Conductivity Reviewed

    Shuhei Higashibayashi, Ryoji Tsuruoka, Yarasi Soujanya, Uppula Purushotham, G. Narahari Sastry, Shu Seki, Takeharu Ishikawa, Shinji Toyota, Hidehiro Sakurai

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   85 ( 4 )   450 - 467   2012.4

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    DOI: 10.1246/bcsj.20110286

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  • Construction of novel molecular architectures from anthracene units and acetylene linkers Reviewed

    Shinji Toyota

    PURE AND APPLIED CHEMISTRY   84 ( 4 )   917 - 929   2012

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    DOI: 10.1351/PAC-CON-11-09-07

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  • Synthesis and redox properties of pi-conjugated 4,5-diazafluorene derivatives incorporating 9-cyanomethylene moiety as an electron acceptor Reviewed

    Katsuya Sako, Yasufumi Mugishima, Tetsuo Iwanaga, Shinji Toyota, Hiroyuki Takemura, Motonori Watanabe, Teruo Shinmyozu, Michito Shiotsuka, Hitoshi Tatemitsu

    TETRAHEDRON LETTERS   52 ( 44 )   5865 - 5868   2011.11

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    DOI: 10.1016/j.tetlet.2011.08.164

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  • Introduction of Two Anthracene Moieties into Perylenebis(dicarboximide) Core by Suzuki-Miyaura Coupling toward Construction of Donor-Acceptor-Donor Arrays Reviewed

    Tetsuo Iwanaga, Hiroko Ida, Makoto Takezaki, Shinji Toyota

    CHEMISTRY LETTERS   40 ( 9 )   970 - 971   2011.9

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    DOI: 10.1246/cl.2011.970

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  • Chemistry of Anthracene-Acetylene Oligomers. XIX. Construction of Higher 1,8-Anthrylene-Alkynylene Macrocycles: Synthesis, Structures, and Conformational Analysis of Cyclic Hexamer and Dodecamer Reviewed

    Shinji Toyota, Hiroaki Harada, Hiroaki Miyahara, Takahiro Kawakami, Kan Wakamatsu, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   84 ( 8 )   829 - 838   2011.8

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    DOI: 10.1246/bcsj.20110121

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  • Chemistry of Anthracene-Acetylene Oligomers. XVIII. Construction and Structures of Belt-Shaped Macrocyclic Oligomers with Anthracene Units and Acetylene Linkers and Resolution of Chiral Derivatives Reviewed

    Takeharu Ishikawa, Tetsuo Iwanaga, Shinji Toyota, Mikio Yamasaki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   84 ( 7 )   729 - 740   2011.7

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    DOI: 10.1246/bcsj.20110066

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  • Structures and Conformational Analysis of 1,8-Bis(9-triptycylethynyl)anthracene and Its Derivatives as Prototypes of Molecular Spur Gears Reviewed

    Shinji Toyota, Takamasa Shimizu, Tetsuo Iwanaga, Kan Wakamatsu

    CHEMISTRY LETTERS   40 ( 3 )   312 - 314   2011.3

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    DOI: 10.1246/cl.2011.312

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  • How to Construct Chiral Macrocycles from Anthracene Units and Acetylene Linkers Reviewed

    Shinji Toyota

    CHEMISTRY LETTERS   40 ( 1 )   12 - 18   2011.1

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  • Synthesis and spectroscopic study of phenylene-(poly)ethynylenes substituted by amino or amino/cyano groups at terminal(s): electronic effect of cyano group on charge-transfer excitation of acetylenic pi-systems Reviewed

    Jing-Kun Fang, De-Lie An, Kan Wakamatsu, Takeharu Ishikawa, Tetsuo Iwanaga, Shinji Toyota, Shin-ichi Akita, Daisuke Matsuo, Akihiro Orita, Junzo Otera

    TETRAHEDRON   66 ( 29 )   5479 - 5485   2010.7

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    DOI: 10.1016/j.tet.2010.05.016

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  • Optical Resolution of Chiral Buckybowls by Chiral HPLC Reviewed

    Ryoji Tsuruoka, Shuhei Higashibayashi, Takeharu Ishikawa, Shinji Toyota, Hidehiro Sakurai

    CHEMISTRY LETTERS   39 ( 6 )   646 - 647   2010.6

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    DOI: 10.1246/cl.2010.646

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  • Influence of Conformation of 9,10-Anthrylene Rotors on Structures and Self-association Properties of Macrocyclic Arylene-Alkynylene Oligomers Reviewed

    Kazuaki Miyamoto, Tetsuo Iwanaga, Shinji Toyota

    CHEMISTRY LETTERS   39 ( 3 )   288 - 290   2010.3

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    DOI: 10.1246/cl.2010.288

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  • Chemistry of Anthracene-Acetylene Oligomers XV. Synthesis, Structures, and Dynamic Behavior of Chiral Anthrylene Ethynylene Cyclic Tetramers and Related Derivatives and Resolution of Enantiomers Reviewed

    Takeharu Ishikawa, Toshiaki Shimasaki, Haruo Akashi, Tetsuo Iwanaga, Shinji Toyota, Mikio Yamasaki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   83 ( 3 )   220 - 232   2010.3

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    DOI: 10.1246/bcsj.20090270

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  • Synthesis and spectroscopic study of diphenylamino-substituted phenylene-(poly)ethynylenes: remarkable effect of acetylenic conjugation modes Reviewed

    Jing-Kun Fang, De-Lie An, Kan Wakamatsu, Takeharu Ishikawa, Tetsuo Iwanaga, Shinji Toyota, Daisuke Matsuo, Akihiro Orita, Junzo Otera

    TETRAHEDRON LETTERS   51 ( 6 )   917 - 920   2010.2

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  • Chemistry of anthracene-acetylene oligomers. XVII. Synthesis, structure, and dynamic behavior of 1,8-anthrylene pentamers and hexamers with acetylene linkers Reviewed

    Shinji Toyota, Takahiro Kawakami, Risa Shinnishi, Rie Sugiki, Shinya Suzuki, Tetsuo Iwanaga

    ORGANIC & BIOMOLECULAR CHEMISTRY   8 ( 21 )   4997 - 5006   2010

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  • Chemistry of Anthracene-Acetylene Oligomers. XIV. Convenient Synthesis of Anthrylethynes by Double Elimination Reaction from Aldehydes and Sulfones Reviewed

    Shinji Toyota, Rie Azami, Tetsuo Iwanaga, Daisuke Matsuo, Akihiro Orita, Junzo Otera

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   82 ( 10 )   1287 - 1291   2009.10

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    DOI: 10.1246/bcsj.82.1287

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  • Chemistry of Anthracene-Acetylene Oligomers. XIII. Synthesis, Structures, and Spectroscopic Properties of All Possible 1,8-Anthrylene Cyclic Tetramers with Acetylene and Diacetylene Linkers Reviewed

    Shinji Toyota, Hiroaki Miyahara, Michio Goichi, Shingo Yamasaki, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   82 ( 8 )   931 - 945   2009.8

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    DOI: 10.1246/bcsj.82.931

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  • Synthesis and spectroscopic study of silacyclyne-substituted phenyleneethynylenes Reviewed

    Guoliang Mao, Akihiro Orita, Daisuke Matsuo, Takayoshi Hirate, Tetsuo Iwanaga, Shinji Toyota, Junzo Otera

    TETRAHEDRON LETTERS   50 ( 24 )   2860 - 2864   2009.6

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    DOI: 10.1016/j.tetlet.2009.03.163

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  • Enantiopure 1,8-Anthrylene Dimer with Acetylene Linkers and an Intraannular Alkyl Group Reviewed

    Shinji Toyota, Hiroyuki Onishi, Kan Wakamatsu, Tetsuo Iwanaga

    CHEMISTRY LETTERS   38 ( 4 )   350 - 351   2009.4

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    DOI: 10.1246/cl.2009.350

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  • Vapour Induced Crystalline Transformation Investigated by ab initio Powder X-ray Diffraction Analysis Reviewed

    Kotaro Fujii, Yasunari Ashida, Hidehiro Uekusa, Shinya Hirano, Shinji Toyota, Fumio Toda, Zhigang Pan, Kenneth D. M. Harris

    CRYSTAL GROWTH & DESIGN   9 ( 2 )   1201 - 1207   2009.2

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    DOI: 10.1021/cg801142p

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  • Molecular Structure of Chlorocycloheptane in Inclusion Compound with 9,9 '-Bianthryl and Gelation during Crystallization Reviewed

    Shinji Toyota, Yohei Okamoto, Takeharu Ishikawa, Tetsuo Wanaga, Masanori Yamada

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   82 ( 2 )   182 - 186   2009.2

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    DOI: 10.1246/bcsj.82.182

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  • Stereogenic Motif Consisting of Rigid Ring and Intraannular Chains: Isolation and Structures of Stereoisomers of 9-Alkyl-1,8-anthrylene - Butadiynylene Cyclic Dimers Reviewed

    Shinji Toyota, Hiroyuki Onishi, Yoshihiro Kawai, Takaaki Morimoto, Hiroaki Miyahara, Tetsuo Iwanaga, Kan Wakamatsu

    ORGANIC LETTERS   11 ( 2 )   321 - 324   2009.1

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  • Chemistry of Anthracene-Acetylene Oligomers. X. Synthesis, Structures, and Properties of 1,8-Anthrylene-Alkynylene Cyclic Trimers Reviewed

    Shinji Toyota, Hiroaki Miyahara, Michio Goichi, Kan Wakamatsu, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   81 ( 9 )   1147 - 1157   2008.9

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    DOI: 10.1246/bcsj.81.1147

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  • Structures and inclusion properties of racemic and enantiopure dimethyl and diphenyl 9,9'-bianthryl-2,2-dicarboxylates Reviewed

    Shinji Toyota, Toshiaki Shimasaki, Shinya Hirano, Makoto Kuga, Fumio Toda

    CHIRALITY   20 ( 3-4 )   295 - 300   2008.3

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  • Molecular folding screen: folding and unfolding of 1,8-anthrylene-ethynylene oligomers by photochemical cycloaddition and thermal cycloreversion Reviewed

    Shinji Toyota, Makoto Kuga, Akiko Takatsu, Michio Goichi, Tetsuo Iwanaga

    CHEMICAL COMMUNICATIONS   ( 11 )   1323 - 1325   2008.3

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  • Papers based on presentations at the 12(th) international symposium on novel aromatic compounds (ISNA-12),22-27 July 2007, Awaji island, Japan - Preface Reviewed

    Shinji Toyota

    PURE AND APPLIED CHEMISTRY   80 ( 3 )   IV - IV   2008.3

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  • Enantiopure anthrylene-ethynylene cyclic tetramer and racemization via rotation of anthracene unit about acetylenic axes Reviewed

    Takeharu Ishikawa, Toshiaki Shimasaki, Haruo Akashi, Shinji Toyota

    ORGANIC LETTERS   10 ( 3 )   417 - 420   2008.2

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    DOI: 10.1021/ol702783v

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  • Chemistry of Anthracene-acetylene oligomers - 7 - New pi-conjugated system with a rigid framework of 1,8-anthrylene-ethynylene cyclic dimer and its monoanthraquinone Analogue Reviewed

    Shinji Toyota, Megumi Kurokawa, Mai Araki, Kazuya Nakamura, Tetsuo Iwanaga

    ORGANIC LETTERS   9 ( 18 )   3655 - 3658   2007.8

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  • Enantiomeric resolution of chiral 1,8-anthrylene cyclic tetramers with acetylene and diacetylene linkers Reviewed

    Michio Goichi, Shingo Yamasaki, Hiroaki Miyahara, Kan Wakarnatsu, Haruo Akashi, Shinji Toyota

    CHEMISTRY LETTERS   36 ( 3 )   404 - 405   2007.3

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    DOI: 10.1246/cl.2007.404

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  • A new organic zeolite created by molecular aggregation of 1,1-bis(3,4-dihydroxyphenyl) cyclohexane in the solid state Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda, Masako Kato, Ingeborg Csoregh

    CRYSTENGCOMM   9 ( 9 )   786 - 792   2007

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    DOI: 10.1039/b705163h

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  • Facile formation of acenaphtho[1,2-a]pyrene structures by thermal isomerization of bis(8-ethynyl-1-naphthyl)ethynes Reviewed

    Shinji Toyota, Keiko Kaneko, Megumi Kurokawa, Kan Wakamatsu

    TETRAHEDRON LETTERS   47 ( 41 )   7349 - 7352   2006.10

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    DOI: 10.1016/j.tetlet.2006.08.011

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  • Construction of strained frameworks with 1,8-anthrylene units and acetylene linkers: Synthesis and structures of cyclic trimers Reviewed

    Michio Goichi, Hiroaki Miyahara, Shinji Toyota

    CHEMISTRY LETTERS   35 ( 8 )   920 - 921   2006.8

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    DOI: 10.1246/cl.2006.920

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  • Chemistry of anthracene-acetylene oligomers - Part 3 - Construction of three-dimensional framework with 1,8-anthrylene and butadiynylene building units: Synthesis and properties of cyclic tetramers Reviewed

    Michio Goichi, Shinji Toyota

    CHEMISTRY LETTERS   35 ( 6 )   684 - 685   2006.6

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    DOI: 10.1246/cl.2006.684

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  • Absolute configuration and chiroptical properties of an enantiopure [5-chloro-2-(dimethylaminomethyl)phenyl]-phenylborane complex Reviewed

    Shinji Toyota, Fumiko Ito, Toshiyuki Yamamoto, Haruo Akashi, Tetsuo Iwanaga

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   79 ( 5 )   796 - 798   2006.5

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    DOI: 10.1246/bcsj.79.796

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  • Chemistry of anthracene-acetylene oligomers: Synthesis and enantiomeric resolution of a chiral 1,8-anthrylene-ethynylene cyclic tetramer Reviewed

    S Toyota, S Suzuki, M Goichi

    CHEMISTRY-A EUROPEAN JOURNAL   12 ( 9 )   2482 - 2487   2006.3

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    DOI: 10.1002/chem.200501111

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  • Solid-state phase transition of an inclusion complex of 5-methyl-2-pyridone with 1,3,5-benzenetricarboxylic acid Reviewed

    Shinya Hirano, Shinji Toyota, Fumio Toda, Kotaro Fujii, Hidehiro Uekuasa

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   45 ( 36 )   6013 - 6016   2006

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    DOI: 10.1002/anie.200600845

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  • Chemistry of anthracene-acetylene oligomers. II. Synthesis, structure, and properties of 1,8-anthrylene-ethynylene cyclic tetramers and related acyclic oligomers Reviewed

    S Toyota, M Goichi, M Kotani, M Takezaki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 12 )   2214 - 2227   2005.12

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    DOI: 10.1246/bcsj.78.2214

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  • Enantiomeric resolution and absolute stereochemistry of stable rotamers of dimethyl 6,6 '-dimethyl-9,9 '-bitriptycyl-2,2 '-dicarboxylate as a stereochemical analog of (R*,R*)- and (R,S)-tartaric acids Reviewed

    S Toyota, A Takau, Y Hitaka, M Oki, K Wakamatsu

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 12 )   2228 - 2234   2005.12

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    DOI: 10.1246/bcsj.78.2228

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  • The important role of solvent vapor in an organic solid state reaction Reviewed

    Seiken Nakamatsu, Shinji Toyota, William Jones, Fumio Toda

    Chemical Communications   ( 30 )   3808 - 3810   2005.8

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    DOI: 10.1039/b503922c

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  • Control of differential inclusion complexation in the solid state by seed crystals Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda, Spyros Chatziefthimiou, Petros Giastas, Irene M. Mavridis, Masako Kato

    Angewandte Chemie - International Edition   44 ( 32 )   5097 - 5100   2005.8

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    DOI: 10.1002/anie.200501364

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  • Improved synthesis of 1,8-diiodoanthracene and its application to the synthesis of multiple phenylethynyl-substituted anthracenes

    M Goichi, K Segawa, S Suzuki, S Toyota

    SYNTHESIS-STUTTGART   2116 ( 13 )   2116 - 2118   2005.8

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    DOI: 10.1055/s-2005-869999

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  • Rotational isomerism involving an acetylenic carbon - VII. Restricted rotation about acetylenic axis in a diphenylethyne derivative with sterically crowded m-terphenyl moieties

    S Toyota, T Yanagihara, Y Yoshida, M Goichi

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 7 )   1351 - 1353   2005.7

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    DOI: 10.1246/bcsj.78.1351

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  • Rotational isomerism involving an acetylenic carbon VI. Syntheses, structures, and dynamic stereochemistry of bis(1-phenyl-9-anthryl)ethynes: Highly restricted rotation about acetylenic axis in acyclic diarylethynes

    T Makino, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   78 ( 5 )   917 - 928   2005.5

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    DOI: 10.1246/bcsj.78.917

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  • Syntheses, spectroscopic properties, and CU(I) complexes of all possible symmetric BI-1,10-phenanthrolines

    S Toyota, A Goto, K Kaneko, T Umetani

    HETEROCYCLES   65 ( 3 )   551 - 562   2005.3

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    DOI: 10.3987/COM-04-10273

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  • A new [2 + 2] photodimerization of 5-chloro- and 5-methyl-2-pyridone in their inclusion complexes with 1,1′-biphenyl-2,2′-dicarboxylic acid as a model for DNA damage by photodimerization of its thymine component Reviewed

    Shinya Hirano, Shinji Toyota, Fumio Toda

    Chemical Communications   ( 5 )   643 - 644   2005.2

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    DOI: 10.1039/b414134b

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  • Isolation of axial conformers of chloro- and bromocyclohexane in a pure state as inclusion complexes with 9,9′-bianthryl, and the discovery of a novel 1,3 diaxial Cl⋯H weak interaction Reviewed

    Hirano S, Toyota S, Kato M, Toda F

    Chemical Communications   ( 29 )   3646 - 3648   2005

  • New [2+2] and [4+4] photodimerizations of 2-pyridones in an inclusion complex with a simple carboxylic acid host: A model of DNA damage by photodimerization of its thymine component Reviewed

    Shinya Hirano, Shinji Toyota, Fumio Toda

    Heterocycles   64   383 - 391   2004.12

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    DOI: 10.3987/COM-04-S(P)39

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  • Substituent effects on configurational stabilities at tetrahedral boron atoms in intramolecular borane-amine complexes: Structures, enantiomeric resolution, and rates of enantiomerization of [2-(dimethylaminomethyl)phenyllphenylboranes

    S Toyota, F Ito, N Nitta, T Hakamata

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   77 ( 11 )   2081 - 2088   2004.11

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    DOI: 10.1246/bcsj.77.2081

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  • Absolute stereochemisty and chiroptical properties of 3,3 '-bis(methoxycarbonyl)-9,9 '-bianthryl

    S Toyota, T Shimasaki, T Ueda, N Tanifuji, K Wakamatsu

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   77 ( 11 )   2065 - 2070   2004.11

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    DOI: 10.1246/bcsj.77.2065

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  • Isolation of equatorial conformers of chloro- and bromocyclohexane in a pure state as inclusion complexes with a host compound Reviewed

    Shinya Hirano, Shinji Toyota, Fumio Toda

    Chemical Communications   10 ( 20 )   2354 - 2355   2004.10

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    DOI: 10.1039/b409905m

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  • Enantiomer separation of rac-2,2′-dihydroxy-1,1′-binaphthyl (BNO) by inclusion complexation with racemic or achiral ammonium salts and a novel transformation of a 1:1:1 racemic complex of BNO, Me4N +·Cl- and MeOH into a conglomerate complex in the solid state Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    Tetrahedron   60 ( 35 )   7767 - 7774   2004.8

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    DOI: 10.1016/j.tet.2004.05.122

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  • A novel transformation of a 1:1:1 racemic complex of 2,2′-dihydroxy- 1,1′-binaphthyl, Me4N+ Cl- and MeOH into a conglomerate in the solid state by heating or contact with MeOH vapour Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    Chemical Communications   10 ( 16 )   1844 - 1845   2004.8

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    DOI: 10.1039/b404297b

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  • Macrocyclic 1,8-anthrylene-ethynylene oligomers: Three-dimensional pi-conjugated architectures Reviewed

    S Toyota, M Goichi, M Kotani

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   43 ( 17 )   2248 - 2251   2004.4

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    DOI: 10.1002/anie.200353647

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  • Versatility in stabilization of crystalline inclusion complexes of a bulky diol host by various closely related acidic and ester guests Reviewed

    Ingeborg Csöregh, Shinya Hirano, Shinji Toyota, Petra Bombicz, Fumio Toda

    CrystEngComm   6   60 - 69   2004.3

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    DOI: 10.1039/b316094g

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  • Enantiomeric resolution of intramolecular amine-borane complex with a chiral boron center

    S Toyota, T Hakamata, N Nitta, F Ito

    CHEMISTRY LETTERS   33 ( 3 )   206 - 207   2004.3

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    DOI: 10.1246/cl.2004.206

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  • Efficient resolution of 2,2′-dihydroxy-1,1′-binaphthyl by inclusion complexation with chiral N-(3-chloro-2-hydroxypropyl)-N,N,N-trimethylammonium chloride Reviewed

    Fumio Toda, Kazuhiro Yoshizawa, Shunji Hyoda, Shinji Toyota, Spyros Chatziefthimiou, Irene M. Mavridis

    Organic and Biomolecular Chemistry   2 ( 4 )   449 - 451   2004.2

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    DOI: 10.1039/b314040g

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  • Acid-catalyzed cyclization reactions of 2,2′ -bis(diarylhydroxymethyl)biphenyls to 5,5,7,7-tetraaryl-5,7-dihydrodibenzo[c,e]oxepins in the solid state

    Shinya Hirano, Shinji Toyota, Fumio Toda

    Heterocycles   62   749 - 756   2004.1

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    DOI: 10.3987/com-03-s(p)73

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  • Absolute conformation revisited: Experimental approach

    M Oki, S Toyota

    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY   2004, 255?267. ( 2 )   255 - 267   2004.1

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  • New [4 + 4] photodimerization of 5-chloro-2-pyridone to the meso-cis-syn dimer as an inclusion complex with 1,2,4,5-benzenetetracarboxylic acid Reviewed

    Shinya Hirano, Shinji Toyota, Fumio Toda

    Mendeleev Communications   14 ( 6 )   247 - 249   2004

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    DOI: 10.1070/MC2004v014n06ABEH002030

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  • Facile dissociation of B-S coordination bonds in [2,6-bis(ethylthiomethyl)phenyl]diethylborane by an S(N)2-type mechanism

    S Toyota, N Uemitsu, M Oki

    HETEROATOM CHEMISTRY   15 ( 3 )   241 - 245   2004

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    DOI: 10.1002/hc.20005

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  • Rotational isomerism involving an acetylenic carbon. Part 5: Restricted rotation about acetylenic axis in sterically crowded bis(1-phenyl-9-anthryl)ethynes

    S Toyota, T Makino

    TETRAHEDRON LETTERS   44 ( 42 )   7775 - 7778   2003.10

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    DOI: 10.1016/j.tetlet.2003.08.079

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  • Experimental and theoretical investigations of absolute stereochemistry and chiroptical properties of enantiopure 2,2 '-substituted 9,9 '-bianthryls

    S Toyota, T Shimasaki, N Tanifuji, K Wakamatsu

    TETRAHEDRON-ASYMMETRY   14 ( 12 )   1623 - 1629   2003.6

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    DOI: 10.1016/S0957-4166(03)00252-0

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  • Preparative and mechanistic studies of solvent-free Rap-Stoermer reactions Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda, Ingeborg Csöregh

    Green Chemistry   5 ( 3 )   353 - 356   2003.6

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    DOI: 10.1039/b303802p

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  • Easy isolation of the enol form of acetylacetone as an inclusion complex with host compounds Reviewed

    Zofia Urbanczyk-Lipkowska, Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    CrystEngComm   5   114 - 116   2003.4

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    DOI: 10.1039/b301386n

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  • Reactivities of Stable Rotamers: XLIV. Ring-Opening Reactions of 1-(9-Fluorenyl)-2-(2-methyl-2-oxiranyl)naphthalene Rotamers with Acids and the Structure of Oxiranes Reviewed

    Michinori Oki, Yoshitaka Toyofuku, Tatsuya Sakaue, Takanori Hirose, Mitsuhiro Asakura, Nobuhiro Morita, Shinji Toyota

    Russian Journal of Organic Chemistry   39 ( 4 )   542 - 553   2003.4

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    DOI: 10.1023/A:1026063919203

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  • Photoreactions of 2- and 4-pyridones in their inclusion crystal with a host compound

    Minoru Yagi, Shinya Hirano, Shinji Toyota, Fumio Toda, Petros Giastas, Irene M. Marvidis

    Heterocycles   59 ( 2 )   735 - 744   2003.3

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    DOI: 10.3987/com-02-s85

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  • Chiral switching and fast reversible molecular movement phenomena in crystals Reviewed

    Shinya Hirano, Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda, Zofia Urbanczyk-Lipkowska

    Mendeleev Communications   13 ( 3 )   141 - 144   2003

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    DOI: 10.1070/MC2003v013n03ABEH001808

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  • Rotational isomerism involving an acetylenic carbon IV: synthesis and structure of bis(1,1 ';3 ',1 ''-terphenyl-2 '-yl)ethynes: molecular design of sterically congested alkynes toward restricted rotation about acetylenic axis

    S Toyota, T Iida, C Kunizane, N Tanifuji, Y Yoshida

    ORGANIC & BIOMOLECULAR CHEMISTRY   1 ( 13 )   2298 - 2302   2003

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    DOI: 10.1039/b302016a

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  • Preparation and separation of all possible rotamers of a stereochemical analog of meso-tartaric acid: optically inactive and optically active isomers of (R,S)-2,2 '-bis(methoxycarbonyl)-6,6 '-dimethyl-9,9 '-bitriptycyl

    S Toyota, T Nakagawa, M Kotani, M Oki, H Uekusa, Y Ohashi

    TETRAHEDRON   58 ( 52 )   10345 - 10351   2002.12

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    DOI: 10.1016/S0040-4020(02)01408-4

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  • Intramolecular C=O center dot center dot center dot B interactions in o-boron substituted benzaldehyde, acetophenone, and benzophenone

    S Toyota, M Asakura, T Sakaue

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   75 ( 12 )   2667 - 2671   2002.12

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    DOI: 10.1246/bcsj.75.2667

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  • Aromatic chemistry

    Shinji Toyota, Masahiko Iyoda, Fumio Toda

    Annual Reports on the Progress of Chemistry - Section B   98   359 - 407   2002

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  • A novel host compound, 9,9-bis(4-hydroxy-3-methylphenyl)fluorene, which binds volatile guests tightly and non-volatile guests loosely Reviewed

    Toda F, Hirano S, Toyota S, Kato M, Sugio Y, Hachiya T

    CrystEngComm   4 ( 31 )   171 - 173   2002

  • Freezing of equilibrium of imidazoles by inclusion crystallization with a host compound: Isolation of the different tautomeric types in a pure state Reviewed

    Yagi M, Hirano S, Toyota S, Kato M, Toda F

    CrystEngComm   4 ( 25 )   143 - 145   2002

  • Efficient solvent-free Thorpe reactions Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    Green Chemistry   4 ( 1 )   68 - 70   2002

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    DOI: 10.1039/b110437n

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  • Solvent-free Claisen and Cannizzaro reactions Reviewed

    Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    Tetrahedron Letters   42 ( 45 )   7983 - 7985   2001.11

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    DOI: 10.1016/S0040-4039(01)01562-3

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  • Effects of aryl and arylethynyl substituents at the 1-position on rotational barrier around C(sp)-C(sp(3)) bonds and bending deformation of acetylenic carbons in bis(9-triptycyl)ethynes

    S Toyota, T Yamamori, T Makino

    TETRAHEDRON   57 ( 17 )   3521 - 3528   2001.4

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    DOI: 10.1016/S0040-4020(01)00232-0

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  • Restricted rotation involving the tetrahedral carbon. Lxiv. Barriers to rotation of s-alkyl groups in 9-s-alkyl-8,13-difluoro-l,4-dimethyland 1,2,3,4-tetrachloro-triptycenes Reviewed

    M. Oki, M. Nishino, K. Kaieda, T. Nakashima, S. Toyota

    Bulletin of the Chemical Society of Japan   74 ( 2 )   357 - 361   2001.2

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    DOI: 10.1246/bcsj.74.357

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  • Trinuclear copper(I)-bipyridine triskelion: Template/bascule control of coordination complex stereochemistry in a trefoil knot precursor

    CR Woods, M Benaglia, S Toyota, K Hardcastle, JS Siegel

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   40 ( 4 )   749 - 751   2001

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    DOI: 10.1002/1521-3773(20010216)40:4<749::AID-ANIE7490>3.0.CO;2-D

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  • Tetranuclear copper(I)-biphenanthroline gridwork: Violation of the principle of maximal donor coordination caused by intercalation and CH-to-N forces

    S Toyota, CR Woods, M Benaglia, R Haldimann, K Warnmark, K Hardcastle, JS Siegel

    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION   40 ( 4 )   751 - 754   2001

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    DOI: 10.1002/1521-3773(20010216)40:4<751::AID-ANIE7510>3.0.CO;2-4

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  • Reactivities of stable rotamers. XLIII. Diazotization of 2-methyl-2-(1,2,3,4-tetrachloro- and 1,4-dimethoxy-9-triptycyl)propylamine rotamers Reviewed

    M. Oki, S. Yoshida, Y. Taguchi, I. Miato, K. Nobuoka, S. Toyota, T. Tanaka, Y. Tanaka, G. Yamamoto

    Bulletin of the Chemical Society of Japan   73 ( 11 )   2563 - 2569   2000.11

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    DOI: 10.1246/bcsj.73.2563

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  • Rotational isomerism involving an acetylenic carbon II: Effect of 1-halogen substituents on rotamer population and rotational barrier around C(sp)-C(sp(3)) bonds in bis(9-triptycyl)ethynes

    S Toyota, T Yamamori, T Makino, M Oki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 11 )   2591 - 2597   2000.11

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  • Structural and stereochemical studies of tris[2-(trifluoromethyl)phenyl]borane: Spontaneous resolution, stereodynamics, and intramolecular C-F center dot center dot center dot B interactions

    S Toyota, M Asakura, M Oki, F Toda

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 10 )   2357 - 2362   2000.10

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  • Absolute conformation and chiroptical properties. VII. 9(1 ')-msc and Psc forms of 9-(2-fluoro-1,1-dimethylethyl)- and 9-(1,1-dimethylpropyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes

    S Toyota, S Yoshida, H Kojima, M Oki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 10 )   2371 - 2376   2000.10

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    DOI: 10.1246/bcsj.73.2371

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  • Benzene-ethene interactions as studied by ab initio calculations

    M Oki, S Takano, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 10 )   2221 - 2230   2000.10

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    DOI: 10.1246/bcsj.73.2221

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  • Rotational isomerism involving an acetylenic carbon: Synthesis of and barrier to rotation around C(sp)-C(sp(3)) bonds in bis(1,4-disubstituted 9-triptycyl)ethynes

    S Toyota, T Yamamori, M Asakura, M Oki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   73 ( 1 )   205 - 213   2000.1

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    DOI: 10.1246/bcsj.73.205

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  • Deprotonation from an N-methyl group in 2-[1-(dimethylamino)-1-methylethyl]phenylborane derivatives

    M Asakura, M Oki, S Toyota

    ORGANOMETALLICS   19 ( 2 )   206 - 208   2000.1

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    DOI: 10.1021/om990724n

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  • Solvent-free robinson annelation reaction Reviewed

    Hisakazu Miyamoto, Shotaro Kanetaka, Koichi Tanaka, Kazuhiro Yoshizawa, Shinji Toyota, Fumio Toda

    Chemistry Letters   ( 8 )   888 - 889   2000

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    DOI: 10.1246/cl.2000.888

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  • Reactivities of stable rotamers. XLII. Generation and fates of rotameric [1-(9-fluorenyl)-2-naphthyl]methyl radicals

    M Oki, T Hirose, K Kaneko, T Hidaka, H Ozaki, M Asakura, S Toyota, T Ishiguro, N Nakamura

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   72 ( 10 )   2327 - 2336   1999.10

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    DOI: 10.1246/bcsj.72.2327

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  • Effect of benzylic methyl groups on kinetic basicity of amine ligand in o-boron substituted N,N-dimethylbenzylamines

    S Toyota, M Asakura, T Futakawa, M Oki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   72 ( 8 )   1879 - 1885   1999.8

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    DOI: 10.1246/bcsj.72.1879

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  • Dimensiosolvatic effects. VI. Rates of ionization of 2-fluoro-4,4,5,5-tetramethyl-1,3-dioxolane: Dimensiosolvatic vs. hydrogen-bond effects

    M Oki, H Ikeda, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   72 ( 6 )   1343 - 1349   1999.6

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    DOI: 10.1246/bcsj.72.1343

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  • Reactivities of stable rotamers, XLI. Reactions of 1-(9-fluorenyl)-2- (1-methylethenyl)naphthalene rotamers with chalcogenyl halides and observation of coloration during the reaction of methanesulfenyl chloride and the ap-rotamer1) Reviewed

    Michinori Oki, Takanori Hirose, Yasukazu Kataoka, Taisuke Ogata, Shinji Toyota, Takashi Matsuo, Yasushi Kawai, Atsuyoshi Ohno

    Bulletin of the Chemical Society of Japan   72 ( 1 )   63 - 72   1999

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    DOI: 10.1246/bcsj.72.63

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  • Camphorsultam - An excellent chiral reagent for enantiomer resolution and determination of absolute stereochemistry

    S Toyota

    ENANTIOMER   4 ( 1 )   25 - 32   1999

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  • Mechanisms of inversion at pyramidal sulfur atoms in three-coordinate sulfur compounds

    S Toyota

    REVIEWS ON HETEROATOM CHEMISTRY   21   139 - 162   1999

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  • Four-Center Six-Electron Interaction versus Lone Pair−Lone Pair Interaction between Selenium Atoms in Naphthalene Peri Positions Reviewed

    Warô Nakanishi, Satoko Hayashi, Shinji Toyota

    The Journal of Organic Chemistry   63 ( 24 )   8790 - 8800   1998.11

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    DOI: 10.1021/jo980885l

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  • Absolute conformation and chiroptical properties. VI. 2,2 ',3,3 '-tetramethoxy-9,9 '-bitriptycyl: A stereochemical analog of 1,2-disubstituted ethane with identical substituents

    S Toyota, A Yasutomi, H Kojima, Y Igarashi, M Asakura, M Oki

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   71 ( 11 )   2715 - 2720   1998.11

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    DOI: 10.1246/bcsj.71.2715

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  • Formation of 3-(m-chlorobenzoyloxy)-2(phenylseleno)propan-1-ol and 2-(m-chlorobenzoyloxy)-3-(phenylseleno)propan-1-ol from a reaction of allyl phenyl selenide with m-chloroperoxybenzoic acid

    T Hirose, N Morita, M Asakura, K Kitahara, S Toyota, M Oki

    TETRAHEDRON LETTERS   39 ( 48 )   8877 - 8880   1998.11

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    DOI: 10.1016/S0040-4039(98)02020-6

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  • 2-Fluoro-4,4,5,5-tetramethyl-1,3-dioxolane: A compound carrying two independent probes for determining rates of formations of contact and solvent-separated ion pairs Reviewed

    Michinori Oki, Hiroshi Ikeda, Shinji Toyota

    Tetrahedron Letters   39 ( 42 )   7729 - 7732   1998.10

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    DOI: 10.1016/S0040-4039(98)01684-0

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  • Experimental and theoretical evidence of an S(N)2-type mechanism for dissociation of B-N coordination bonds in 2,6-bis((dimethylamino)methyl)phenylborane derivatives

    S Toyota, T Futawaka, M Asakura, H Ikeda, M Oki

    ORGANOMETALLICS   17 ( 19 )   4155 - 4163   1998.9

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    DOI: 10.1021/om9803974

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  • Dimensiosolvatic Effects. IV. Topomerization in Alkyl α-Chlorobenzyl Ethers and Insights into Mechanisms of Their Thermolyses Reviewed

    Michinori Öki, Hiroshi Ikeda, Hiromichi Miyake, Hirohito Mishima, Shinji Toyota

    Bulletin of the Chemical Society of Japan   71 ( 4 )   915 - 926   1998

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    DOI: 10.1246/bcsj.71.915

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  • Dimensiosolvatic effects. V. Rates of dissociation of ammonium salts derived from tertiary amines and related compounds in solvents with t-alkyl group

    Michinori Oki, Tatsuya Ozaki, Hiroshi Ikeda, Michio Matsusaka, Hirohito Mishima, Masao Koumura, Shinji Toyota

    Russian Journal of Organic Chemistry   34 ( 11 )   1538 - 1548   1998

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  • Synthesis of Unsymmetrical 2,8- and 2,9-Dihalophenanthroliens and Derivatives.(共著)

    Tetrahedron Lett.   39 ( 13 )   1697 - 1700   1998

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  • Dimensiosolvatic Effects, III. Quantification of Dimensiosolvatic Effects by Solvolyses of 2-Bromoadamantane in Water-Alcohol Mixtures Reviewed

    Michinori Oki, Hiroshi Ikeda, Shinji Toyota

    Bulletin of the Chemical Society of Japan   71 ( 3 )   749 - 754   1998

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    DOI: 10.1246/bcsj.71.749

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  • Effects of solvent molecular size on rates of topomerization in organolithium compounds

    M Oki, H Ikeda, K Kodama, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   70 ( 11 )   2791 - 2799   1997.11

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    DOI: 10.1246/bcsj.70.2791

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  • Synthesis and structures of all possible Cr(CO)(3) complexes of triptycene

    S Toyota, H Okuhara, M Oki

    ORGANOMETALLICS   16 ( 18 )   4012 - 4015   1997.9

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    DOI: 10.1021/om9703705

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  • Manifestation of a (distorted) trigonal pyramidal structure of a quadrivalent carbon

    T Hirose, N Morita, S Toyota, M Oki

    TETRAHEDRON LETTERS   38 ( 26 )   4575 - 4578   1997.6

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    DOI: 10.1016/S0040-4039(97)00977-5

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  • Reactivities of stable rotamers .40. Reactions of ap- and sp-1-(9-fluorenyl)-2-(1-methylethenyl)naphthalene rotamers with bromine chloride or iodine chloride and unusual populations of the corresponding 1-(9-fluorenyl)-2-[(E)-2-halo-1-methylethenyl]naphthalene rotamers

    M Oki, T Hirose, K Maeda, M Yanagawa, Y Kataoka, H Kojima, N Morita, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   70 ( 4 )   859 - 868   1997.4

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    DOI: 10.1246/bcsj.70.859

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  • Reactivities of stable rotamers .39. Thermal decomposition of t-butyl 3-methyl-3-(substituted 9-triptycyl)peroxybutanoate rotamers

    M Oki, Fujino, I, D Kawaguchi, K Chuda, Y Moritaka, Y Yamamoto, S Tsuda, T Akinaga, M Aki, H Kojima, N Morita, M Sakurai, S Toyota, Y Tanaka, T Tanuma, G Yamamoto

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   70 ( 2 )   457 - 469   1997.2

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    DOI: 10.1246/bcsj.70.457

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  • Absolute conformation and substituent effects on chiroptical properties of 9-(2-halo-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes

    S Toyota, T Akinaga, H Kojima, M Aki, M Oki

    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY   118 ( 46 )   11460 - 11466   1996.11

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    DOI: 10.1021/ja961520q

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  • Restricted rotation involving the tetrahedral carbon .63. Endeavor toward enhancing the rotational barrier in 9-s-alkyltriptycenes

    M Oki, T Fukuda, M Asakura, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   69 ( 11 )   3267 - 3272   1996.11

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    DOI: 10.1246/bcsj.69.3267

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  • Reactivities of stable rotamers .38. Reaction of chlorine with 1-(9-fluorenyl)-2-(1-methylethenyl)naphthalene rotamers: Outstanding solvent effects on product distribution and Ritter type reactions in acetonitrile

    M Oki, T Hirose, M Aki, N Morita, E Nose, Y Kataoka, M Ono, S Toyota

    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN   69 ( 11 )   3345 - 3353   1996.11

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    DOI: 10.1246/bcsj.69.3345

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  • Structure of bis[8-(phenylselanyl)naphthyl] diselenide: first linear alignment of four Se atoms as a four-centre six-electron bond Reviewed

    War? Nakanishi, Satoko Hayashi, Shinji Toyota

    Chemical Communications   ( 3 )   371 - 371   1996

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    DOI: 10.1039/cc9960000371

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  • Synthesis and structure of 1,4-dimethoxy and 1,4-dimethyl-9-(trifluoromethyl)triptycenes Reviewed

    S. Toyota, Y. Watanabe, H. Yoshida, M. Oki

    Bulletin of the Chemical Society of Japan   68 ( 9 )   2751 - 2756   1995.9

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    DOI: 10.1246/bcsj.68.2751

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  • Dynamic NMR as a Nondestructive Method for Determination of Rates of Dissociation. XXI. Dissociation in 1-(1-Haloethyl)pyrrolium Cations.

    Sigalov Mark V., Toyota Shinji, Oki Michinori, Trofimov Boris A.

    Bull. Chem. Soc. Jpn.   67 ( 4 )   1161 - 1169   1994

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    Topomerization observed for the isopropyl-methyls in the title compounds was reinvestigated with use of the total line shape analysis of NMR spectra. It was found that deprotonation from the pyrrolium cation preceded and was an independent step from the topomerization but the former strongly affects kinetic parameters for the latter process in the presence of excessive hydrogen halide. The extent of the excessiveness of hydrogen halide in the system also affects the reaction rates and the effects were discussed on the standpoint of activation parameters. The rates of topomerization of the isopropyl-methyls were found to be identical with the rates of enantiomerization at the 1-substituent in 1-(1-bromopropyl)-3-isopropyl-2-phenylpyrrolium ion to suggest that the topomerization in other compounds was also attributed to the ionization at the 1-substituent. The results suggest that a 1-pyrrolyl group assists ionization of 1-pyrrolylmethyl halide more effectively than a phenyl group in benzyl halide. This was reproduced by ab initio calculations.

    DOI: 10.1246/bcsj.67.1161

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  • Addition of Hydrogen Halides to 1,2-Dialkylpyrrolium Cations.

    Sigalov Mark V., Toyota Shinji, Oki Michinori, Trofimov Boris A.

    Bull. Chem. Soc. Jpn.   67 ( 7 )   1872 - 1878   1994

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    Although it is believed that addition of an acid to 2-substituted pyrroles produces 5-protonated pyrrolium ions and further reaction is prevented by the stability of the product, this work shows that further addition of hydrogen halides takes place to the pyrrolium ion to produce 2-substituted 4-halo-4,5-dihydro-3H-pyrrolium ions in general. In the case where the 1-alkyl group is a 1-bromoethyl, addition of hydrogen bromide gives one stereoisomer preferentially, of which conformation was determined by NOE experiments to be two C–Br bonds anti with each other, relative stereochemistry being R*and S*. The results are discussed on the thermodynamic stability and/or the kinetic preferences of the products. Generality of the addition of hydrogen bromide to the pyrrolium ion was tested with 1,2-dimethylpyrrole, which gave a kinetically favored isomeric addition product that isomerized to a thermodynamically favored 4-bromo-1,2-dimethyl-4,5-dihydro-3H-pyrrolium bromide on standing.

    DOI: 10.1246/bcsj.67.1872

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  • Effects of Solvent Molecular Size on Dissociation Rates of the N-H Bond in Ammonium Salts Derived from Tertiary Amines

    OKI Michinori, MATSUSAKA Michio, MISHIMA Hirohito, TOYOTA Shinji

    Chemistry Letters   1993 ( 7 )   1249 - 1252   1993.7

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    Rates of dissociation of the N–H bond in ammonium salts derived from tertiary amines were found to be enhanced in solvents of which molecular size is large with respect to those in solvents of small molecular size, if polarities of the solvents are about the same. The effects are attributed to the weak solvation by the solvents of large molecular size which is associated with small positive entropy of activation. Thus the third aspect of solvent effects, bulkiness of solvent molecules, is proposed.

    DOI: 10.1246/cl.1993.1249

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  • Reactivities of Stable Rotamers. XXXI. Bromine Addition to the Olefinic Moiety of Rotameric 1-(9-Fluorenyl)-2-(1-methylethenyl)naphthalenes.

    Oki Michinori, Shionoiri Katsumi, Otake Katsumasa, Ono Masaru, Toyota Shinji

    Bull. Chem. Soc. Jpn.   66 ( 2 )   589 - 597   1993

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    Reaction of bromine with the ap form of the title compound afforded a normal addition compound, whereas the same with the sp form did no addition compound but a pair of bromo-olefins and a cyclized product, formation of which can be rationalized by deprotonation from and by attack of the π-system of the fluorene group on the intervening cation. The abnormal reactions of the sp form are the consequence of the steric effects of the fluorene moiety that prohibits the formation of the tetrahedral carbon at the reaction site. The stereochemistry of the cyclized product was determined both by NOE experiments and by X-ray crystallography. The stereoselective formation of only one isomer was rationalized by the structure of the starting material, of which stereodynamics was studied by the dynamic NMR method, and the direction of the attack of the bromine cation. For comparison of the fate of the intervening cation, the adduct from the ap form was treated with silver p-toluenesulfonate. It was found that the ratios of olefin formation were different from one rotamer to another. The results are discussed on the basis of different degree of openness of the intervening bromonium cation with reference to the same reaction for (1,2-dibromo-1-methylethyl)benzene.

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  • Reactivities of stable rotamers. XXXII. chlorodecarboxylation of 3-(1,4- dimethyl-9-triptycyl)-3-methylbutanoic acid rotamers Reviewed

    M. Oki, Y. Taguchi, T. Okamoto, T. Miyasaka, K. Hamada, S. Toyota, K. Yonemoto, G. Yamamoto

    Bulletin of the Chemical Society of Japan   66 ( 12 )   3790 - 3796   1993

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    DOI: 10.1246/bcsj.66.3790

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  • Syntheses of and restricted Csp3-Csp2 bond rotation in triptycenes that carry C4-olefïnic substituent at 9-position

    Michinori Oki, Yasushi Taguchi, Shinji Toyota

    Bulletin of the Chemical Society of Japan   65 ( 10 )   2616 - 2623   1992.10

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    DOI: 10.1246/bcsj.65.2616

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  • Reactivities of stable rotamers. Part 30. Bromine addition to rotameric 1-(9-fluorenyl)-2-(1-methylvinyl)naphthalene. Fate of intermediate cations produced by bromine cation attack.

    Oki Michinori, Shionoiri Katsumi, Otake Katsumasa, Ono Masaru, Toyota Shinji

    Chemistry Letters   ( 4 )   597 - 600   1991

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    Treatment of the rotamers of the title compound with bromine afforded a normal addition compound in the case of ap, whereas the sp rotamer did bromo-olefins and a cyclic compound only. The results are discussed on the basis of the steric effects and π-participation of the fluorene ring in the case of sp that is not possible in the case of ap. Cation was produced from the bromine adduct of the sp form and the fate of the cation is disucssed by comparing with that of the ap.

    DOI: 10.1246/cl.1991.597

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  • Rotamer populations and molecular structure of 9-isobutyl-1,4-dimethoxytriptvcene: Further evidence for the presence of CH3...O hydrogen bond.

    Oki Michinori, Takiguchi Naoyoshi, Toyota Shinji, Yamamoto Gaku, Murata Shigeru

    Bull. Chem. Soc. Jpn.   61 ( 12 )   4295 - 4302   1988

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    1H NMR spectra of the title compound at low temperatures show the presence of the sc conformer as a major constituent: ΔH°=0.9±0.3 kcal mol−1, ΔS°=5±2 cal mol−1 for the sc\rightleftarrowsap equilibrium. The line shape analysis of the spectra at various temperatures afforded the following activation parameters for the internal rotation about the C9–Ci-Bu bond: ΔHneweq=8.8±0.3 kcal mol−1, ΔSneweq=−5.0±1.2 cal mol−1 K−1 for the apsc process. X-Ray crystallography of the compound revealed that the molecule exists as sc conformers in the crystal. One of the methyl groups of the isobutyl group that directs inward relative to the triptycene skeleton, is placed very closely to the 1-methoxy-oxygen to indicate the presence of the CH3···O hydrogen bond. Implications of other structural parameters are also discussed.

    DOI: 10.1246/bcsj.61.4295

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  • Determination of rates of dissociation of an olefin ligand in an olefin-platinum complex by dynamic NMR spectroscopy.

    Toyota Shinji, Oki Michinori

    Chemistry Letters   ( 1 )   199 - 202   1987

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    Language:English   Publisher:The Chemical Society of Japan  

    The double-doublet signal due to isopropyl-methyl protons in trans-dichloro(4-methyl-1-pentene)(4-methoxycarbonylpyridine 1-oxide)platinum(II) shows the change in line shapes at high temperatures in its 1H NMR spectra, owing to the racemization process, which involves the dissociation of the olefin. The activation parameters were obtained for CDBr3 solutions as follows: ΔH 17.6±0.5 kcal mol−1, ΔS −2.7±1.3 cal mol−1 K−1. Incidentally, this is the first observation of the racemization of an olefin-metal complex by the dynamic NMR method.

    DOI: 10.1246/cl.1987.199

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Books

  • スキルアップ有機化学 : しっかり身につく基礎の基礎

    Elliott, Mark C., 岩澤, 伸治, 豊田, 真司

    東京化学同人  2024.2  ( ISBN:9784807920549

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    Total pages:xviii, 234p   Language:Japanese  

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  • 構造有機化学 : 基礎から物性へのアプローチまで

    中筋, 一弘, 久保, 孝史, 鈴木, 孝紀, 豊田, 真司

    東京化学同人  2020.1  ( ISBN:9784807909575

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    Total pages:x, 302p, 図版 [2] p   Language:Japanese  

    CiNii Books

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  • 有機化合物のスペクトルによる同定法演習編 (第8版)

    岩澤 伸治, 豊田 真司, 村田 滋( Role: Joint author)

    東京化学同人  2018.2  ( ISBN:4807909231

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    Total pages:158  

    ASIN

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  • クライン有機化学 下

    Klein David R, 秋山 隆彦, 岩澤 伸治, 市川 淳士, 金井 求, 後藤 敬, 豊田 真司, 林 高史

    東京化学同人  2018.1  ( ISBN:9784807909049

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    Language:Japanese  

    CiNii Books

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  • クライン有機化学 上

    Klein David R, 秋山 隆彦, 岩澤 伸治, 市川 淳士, 金井 求, 後藤 敬, 豊田 真司, 林 高史

    東京化学同人  2017  ( ISBN:9784807909032

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    Language:Japanese  

    CiNii Books

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  • 有機化合物のスペクトルによる同定法 (第8版)

    岩澤 伸治, 豊田 真司, 村田 滋( Role: Joint translator ,  Original_author: Robert M. Silverstein, Francis X. Webster, David J. Kiemle)

    東京化学同人  2016.12  ( ISBN:4807909169

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    Total pages:441  

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  • 構造有機化学 (朝倉化学大系)

    戸部 義人, 豊田 真司( Role: Joint author)

    朝倉書店  2016.9  ( ISBN:4254146345

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    Total pages:292  

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  • 有機化学演習 III(化学演習シリーズ8)

    豊田 真司( Role: Sole author)

    東京化学同人  2016.6  ( ISBN:4807908839

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    Total pages:237  

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  • 有機化学演習–基本から大学院入試まで−

    山本 学, 豊田 真司, 伊与田 正彦( Role: Joint author)

    東京化学同人  2008.4  ( ISBN:4807906577

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    Total pages:287  

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  • ラウドン有機化学 下

    Loudon G. Marc, Parise Jim, 後藤 敬, 豊田 真司, 箕浦 真生, 村田 滋, 山本 学

    東京化学同人  2019.1  ( ISBN:9784807909445

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    Language:Japanese  

    CiNii Books

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  • ラウドン有機化学(上)

    山本 学, 後藤 敬, 豊田 真司, 箕浦 真生, 村田 滋( Role: Joint translator ,  Original_author: Marc Loudon, Jim Parise)

    東京化学同人  2018.3  ( ISBN:4807909436

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    Total pages:650  

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  • マーチ有機化学(訳書・分担)

    丸善  2003 

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  • 有機立体化学 (シリーズ有機化学の探険)

    豊田 真司( Role: Sole author)

    丸善  2002.12  ( ISBN:4621071335

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    Total pages:180   Language:Japanese  

    CiNii Books

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  • 立体化学入門―三次元の有機化学

    豊田 真司( Role: Sole translator ,  Original_author: M.J.T. ロビンソン)

    化学同人  2002.8  ( ISBN:4759809104

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    Total pages:154   Language:Japanese  

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  • 溶媒分子の大きさ(共著)

    現代化学増刊26有機反応論の新展開 出版社 東京化学同人  1995 

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Awards

  • 基礎有機化学会賞

    2024.9  

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  • 有機π電子系学会賞

    2021  

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  • 長瀬研究振興賞

    2019.4  

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  • 有機合成化学協会中国四国支部奨励賞

    2003  

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    Country:Japan

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Research Projects

  • New developments in aromatic architect: optimization of structures and spaces and created by pi-conjugated systems and functionalization

    Grant number:23H01944  2023.4 - 2027.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

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    Grant amount:\18720000 ( Direct Cost: \14400000 、 Indirect Cost:\4320000 )

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  • Aromatic architect: design of structures and spaces created by pi-conjugated systems and developments of their functions

    Grant number:20H02721  2020.4 - 2024.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

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    Grant amount:\17290000 ( Direct Cost: \13300000 、 Indirect Cost:\3990000 )

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  • 特異な環状構造をもつパイ共役系アントラセン化合物の創製

    2014 - 2016

    文部科学省  科学研究費補助金(基盤研究(C)) 

    豊田 真司

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\5070000 ( Direct Cost: \3900000 、 Indirect Cost:\1170000 )

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  • 反応集積化による芳香族アセチレンの高効率合成と機能の高度化

    2012 - 2013

    文部科学省  科学研究費補助金(新学術領域研究(研究領域提案型)) 

    豊田 真司

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\6630000 ( Direct Cost: \5100000 、 Indirect Cost:\1530000 )

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  • 集積アルキニル化による機能性芳香族アセチレンの高効率合成

    2010 - 2011

    文部科学省  科学研究費補助金(新学術領域研究(研究領域提案型)) 

    豊田 真司

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\6630000 ( Direct Cost: \5100000 、 Indirect Cost:\1530000 )

    複数のエチニル化反応を集積することにより、機能性エチニルアントラセン誘導体の合成法の効率化に取り組んだ。発光および光応答機能が期待される非対称置換9,10-ビス(フェニルエチニル)アントラセン(BPEA)誘導体を標的化合物とした。10-プロモ-9-アントラアルデヒドに対してフェニルエチンとのSonogashiraカップリング続いてベンジルスルホン誘導体とのワンショット二重脱離反応(同一時空間集積)を行うと、高い全収率で目的化合物が得られた。反応の順番を逆にしても良好な結果が得られた。2つの反応をワンポット法(時間集積)で行うために反応条件を最適化した結果、Sonogashiraカップリングの反応溶液に二重脱離の試薬を一挙に加えると反応が円滑に進行した。以上の方法により、一方のフェニル基にメチル、ブロモ、ニトロ基などの置換基をもつ新規非対称BPEA誘導体を効率的に合成することに成功した。これらの反応をさらに組み合わせて、共役を伸長したBPEA誘導体およびBPEAオリ

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  • New developments in aromatic architect: optimization of structures and spaces and created by pi-conjugated systems and functionalization

    Grant number:23K26637  2023.4 - 2027.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B)

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    Grant amount:\18720000 ( Direct Cost: \14400000 、 Indirect Cost:\4320000 )

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  • Synthesis and functional development of curved pi-conjugated compounds with sp3 carbon center

    Grant number:16K17867  2016.4 - 2019.3

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Young Scientists (B)

    Tsurumaki Eiji, TOYOTA Shinji, KAWAMURA Masahiko, NAGAOKA Maiko, FUJISE Kei

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    Grant amount:\4290000 ( Direct Cost: \3300000 、 Indirect Cost:\990000 )

    Various reactions on anthracene derivatives were investigated for the purpose of constructing novel polycyclic aromatic hydrocarbons with a curved structure. Oxidative condensation reaction (Scholl reaction) of di-1-anthryl ketone proceeds at the 9, 9'-position of anthracene ring to give the corresponding product varing a seven-membered ring. On the other hand, Scholl reaction of di-1-anthryl ketone with mesityyloxy groups under the same reaction conditions gave doubly cyclized product accompanied by rearrangement of carbonyl group as a major product. In addition, we applied the oxidative condensation reaction of anthracene analogues to establish an efficient synthetic method of rubicenes.

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  • Intelligent Molecular Design of Spur-Type Molecular Gears with Triptycene Frameworks

    Grant number:22550048  2010 - 2012

    Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research(基盤研究(C))  Grant-in-Aid for Scientific Research (C)

    Shinji TOYOTA

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4680000 ( Direct Cost: \3600000 、 Indirect Cost:\1080000 )

    We designed molecular gears with two or more three-toothedtriptycene frameworks attaching to an anthracene base. The target compounds weresynthesized by cross coupling reactions of 1,8-diiodoanthracenes and 9-ethynyltriptycenederivatives. We evaluated the effects of linker lengths, distances between the axes, andgear shapes on the gear parallel nature based on molecular structures examined by X-rayanalysis and DFT calculations. The dynamic behavior of these compounds was observed byvariable temperature NMR measurements to discuss their rotation mechanism.

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  • Design of Novel Stereoisomers by Using Narrow Space in π-System Rigid Frameworks

    Grant number:19550054  2007 - 2009

    Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research(基盤研究(C))  Grant-in-Aid for Scientific Research (C)

    Shinji TOYOTA

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    Grant amount:\4550000 ( Direct Cost: \3500000 、 Indirect Cost:\1050000 )

    We designed rigid cyclic compounds consisting of anthracene units and acetylene (or diacetylene) linkers as new π-conjugated compounds. Substituents were introduced at inner congested positions, and we isolated some novel stereoisomers (diastereomers and enantiomers) based on the steric hindrance between the ring framework and the intraannular substituents. The structures and dynamic behavior of these isomers were investigated by X-ray analysis, NMR spectra, and DFT calculations. We propose a new concept of stereochemistry through this molecular design.

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  • 芳香環-アセチレン共役系オリゴマーの設計と高度分子変換

    2007 - 2008

    文部科学省  科学研究費補助金(特定領域研究) 

    豊田 真司

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\4300000 ( Direct Cost: \4300000 )

    新しいパイ共役系化合物として芳香環(とくにアントラセン)とアセチレンを交互に連結したオリゴマーを設計し, それらを効率的に合成するための高度分子変換法を探求した. 前年度に確立した方法により合成したビルディングユニットを用いて, 以下の3項目の研究を行った.1. アルキンカップリング反応Sonogashiraカップリングによるアルキン合成では, 水素雰囲気下の反応が副反応を抑制し目的化合物の収率向上に有効であることを見いだした. ブロモアルキンと末端アルキンのカップリングの条件を最適化し, 非対称ジアセチレン誘導体への変換効率を向上させた. アセチレンのホモカップリングでは, Pd触媒酸化的カップリングとCu触媒Eglintonカップリングの適用範囲と限界を明らかにした.2. 二重脱離反応による種々のアントリルエチンの合成スルホンとアルデヒドを用いたワンショット法による二重脱離反応を行い, 1-および9-アントリル基をもつ対称・非対称ジアントリルエチンの簡便合成

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  • アントアセン?アセチレンオリゴマーの化学

    2002

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  • Construction and Application of Chiral Space with Axially Asymmetric Bianthryls

    Grant number:13640550  2001 - 2003

    Ministry of Education, Culture, Sports, Science and Technology  Grants-in-Aid for Scientific Research(基盤研究(C))  Grant-in-Aid for Scientific Research (C)

    Shinji TOYOTA

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\3300000 ( Direct Cost: \3300000 )

    New axially chirai aromatic compounds were designed based on the structure of 9,9'-bianthryl, and their chiroptical properties, features of chiral spaces in crystals, and dynamic stereochemistry were studied.1.Chiral 9,9'-bianthryldicarboxylic acid derivatives, Enantiomers of 2,2'-or 3,3'-dicarboxylic acid derivatives were resolved via diastereomeric salts. The absolute stereochemistry about the chiral axis was determined by the X-ray structural analysis. The observed circular dichroism(CD) spectra were reasonably reproduced by the TDDFT method. The inclusion experiments were carried out for the 2,2'-dicarbocxylie esters. The enantiopure methyl ester includes a wide range of smalt organic molecules, while the racemic compound includes only benzene, The corresponding phenyl ester showed no inclusion ability. These differences are discussed on the basis of X-ray structures.2.Optically active 9,9'-bitriptycyl rotamers. Optically inactive and active rotamers of substituted 9,9'-bitriptycyls were isolated as a stereochemical model of meso-tartaric acid. We revisited the term of "absolute conformation" through this study.3.Restricted rotation about acetylenic axis, To restrict the rotati

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  • Creation of Enantioselective Cross- Coupling Reactions in the Solid State

    Grant number:13640595  2001 - 2002

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (C)

    TODA Fumio, TOYOTA Shinji

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    Grant amount:\3400000 ( Direct Cost: \3400000 )

    Firstly, various organic neactions were carried out in the solid state in order to develop organic solid state reactions. When substrate and / or reagent is liquid, reaction between them was carred out under solvent-free conditions. Sililation reaction of alcohols proceeded efficriently just by mixing of alcohol and trialkylsilyl chloride. Claisen, Thorpe and Cannizzaro reactions were also found to proceed efficiently under solvent-free conditions. Cross-Claisen and Thorpe reactions were also successful. By monitoring of a solvent-free Thorpe reaction by continuous measurements of IR spectra, reaction intermediate was detected and reaction mechanism was clarified. Real solid state reaction is also effective. For example, FeCIa-catalyzed coupling reaction of 2-naphthol proceeded in the solid state very efficiently and its dimer 2, 2' -dihydroxy- 1, -binapthyl was obtained in good yield. However, coss-coupling reaction of 2-naphthol and 1, 2 -naphthalenediol in the solid state gave a complex mixture. Inclusion complexation of two different guest molecules by a host to give an interesting complex consisted of three different components. Unfortunately, however, cross-coupling reaction of the two tautomers was unsuccessful. When chiral host is used for such the cross-coupling reaction in the solid state, enantioselective solvent-free cross-coupling reaction can be accomplished. We are going to design such the dreamy reaction

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  • アントラセンの構造的特徴を活かした分子設計

    1998

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  • 二つのトリプチシル基間のπ系相互作用

    1998

    文部科学省  科学研究費補助金(特定領域研究(A)) 

    豊田 真司

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    Authorship:Principal investigator  Grant type:Competitive

    Grant amount:\2200000 ( Direct Cost: \2200000 )

    トリプチシル基間同士の電子的または立体的なπ系相互作用に関連して,非常に嵩高い9-トリプチシル基を2個有する以下の2系列の分子の構造を立体化学的見地から研究した.「9,9'ビトリブチシル誘導体の光学活性回転異性体の絶対配座」本化合物の非常に高いC9-C9'結合の回転障壁を利用して,1,2-同種二置換エタンの立体化学的モデルである2,2',3,3'-テトラメトキシ化合物のキラル配座異性体の光学活性体の合成に成功した.分子の基本骨格はDicls-Alder反応を用いて構築し,キラルなsc異性体の光学分割はカンファ一試薬を用いたジアステレオマー法で行った.関連化合物のX線構造解析により,この化合物の絶対立体配座は(+)-Psc,(-)-Mscと決定できた.これはap-体がC2hの高い対称性を有するエタン型分子でも,scの配座になれば光学活性になれることを実証したもので,旧来の回転異性を無視した概念を打破するものである.「ジ(9-トリブチシル)アセチレンの回転異性」トリプチシル基の立体障害によりアセチ

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  • Study on Dynamic Molecular Behaviors in Crystal

    Grant number:09044091  1997 - 1999

    Japan Society for the Promotion of Science  Grants-in-Aid for Scientific Research  Grant-in-Aid for Scientific Research (B).

    TODA Fumio, MIYAMOTO Hisakazu, TANAKA Koich, TOYOTA Shinji

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    Grant amount:\6800000 ( Direct Cost: \6800000 )

    When crystals of diallene derivative (A) is heated for 1h, dimethylencecyclobutene derivative (B) is produced by a cyclization reaction. Since A has a s-trans structure on crystal, isomenzation reaction from the s-trans configuration to a s-cis one should be occurred before the cyclization reaction. It is very interesting that such the big molecular motion occurs in a small space of crystal. It was also confirmed that the thermal conversion proceeds stereoselectively.
    When a prochiral molecule is included in a chiral host compound, the former is arranged in a chiral form in its inclusion crystal and its inadiation gave optically active photoreaction product. In most cases of the photoreaction in crystal, crystalline lattice of the inclusion compound is destroyed as the reaction proceeds. On the contrary, photodimerzation of cyclohexenone, coumarin, and thiocoumarin in inclusion complex crystal with optically active host compound proceeded from single-crystal-to-single-crystal and enantioselectively to give corresponding optically active dimer. These reactions were studied by X-ray analysis.
    Some other organic solid state reactions were also developed. For example, Dieckmann reaction, azomethine formation reaction, and Michael addition reaction were found to proceed efficiently in the solid state. Of these reactions, azomethine formation reaction was studied carefully by AFM method.
    Solvent-free reactions were also clarified to proceed selectively. For example, treatment of stilibene and chalcone with pyridine-HBr-BrィイD22ィエD2 salt in the solid state gave meso- and erythro- addition product, respectively. These data clearly show that molecules in crystal move easily and that reaction occurs selectively and efficiently in the solid state.

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  • Rotational Isomerism of Acetylene Compounds

    1997

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  • アセチレン化合物の回転異性

    1997

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  • 分子内硫黄配位子で安定化された有機銅化合物の合成と反応性

    Grant number:07216273  1995

    日本学術振興会  科学研究費助成事業  重点領域研究

    豊田 真司

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    Grant amount:\1500000 ( Direct Cost: \1500000 )

    分子内スルフィド硫黄配位子により安定化されたアリール銅誘導体を合成し、反応性有機銅分子の中間体モデルとしての興味から安定性・反応性を中心に化合物の性質を詳しく調べ、以下の成果を得た。
    有機銅化合物の合成は有機リチウム化合物とハロゲン化銅_<(1)>の反応により行なった。オルト(アルキルチオメチル)フェニル銅は不安定で単離することはできなかったが、オルト位の置換基をアルキルチオ基にしたところ安定性が増大し相当するフェニル銅が不溶性赤茶色固体と可溶性橙色結晶の二つの安定な形態で得られた。分析データから、前者は塩を含まない単純なフェニル銅、後者はフェニル銅とハロゲン化銅_<(1)>の2:1錯体であることが判明した。両方の化合物とも固体では非常に安定であるが、溶液(懸濁液)中では徐々に分解し加水分解生成物を与える。熱分解では加水分解生成物と二重化生成物のビフェニル誘導体がほぼ同じ割合で生成した。塩化アシルとの反応では、可溶性化合物のみが交差カップリングを低収率ながら与えた。硫黄配位子の導入により反応性は低下したものの、上記の反応性は有機銅化合物に典型的なものである。また、化合物の溶解性も反応性に大きな影響を与えることがわかった。
    分子内の種々の位置に配位子を導入した5種類の有機銅化合物の合成し、配位子の配置が安定性に及ぼす影響を検討した。オルトベンジル位に2個の配位子を持つフェニル銅誘導体では、2位と6位にエチルチオメチル基を持つ化合物がどうにか単離できただけであった。ペリ位にエチルチオ基をもつ1-ナフチル銅も不安定であったことを考慮すると、銅原子から5員環の位置にある硫黄配位子の安定化への寄与が小さいことがわかる。一方、オルト[2-(エチルチオ)エテルチオ]フェニル銅は安定な化合物で、溶解性が高い分配位子が1個の化合物より求電子試薬との反応性が高くなった。

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  • 分子内に2個のアミン配位子を持つ有機ホウ素錯体の合成・構造および動的挙動

    Grant number:06740497  1994

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    豊田 真司

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    Grant amount:\900000 ( Direct Cost: \900000 )

    分子内に2個のアミン配位子を持つ有機ホウ素錯体として、2,6-ビス(ジメチルアミノメチル)フェニルボロン酸エステエルを合成し、分子の構造と動的挙動を調べた。この化合物は立体障害が大きいため合成が困難であることが予想されたが、ベンゼン誘導体にアミン-ホウ素の順番に置換基を導入する方法で効率よく目的化合物を得ることができた。
    錯体の温度可変NMRの測定から、溶液中ではホウ素原子に対して2個のアミン配位子が相互に配位-解離を繰り返すような過程、「配位子のスイッチング」が非常に速く起こっていることが判明した。この実験事実は、ホウ素上の置換がS_N2的機構で進行していることを意味しており、ホウ素の反応機構に新しい概念を導入するものである。この種の機構の正当性は、モデル反応の分子軌道計算によっても確かめられた。
    エステル部の置換基の異なる2種類の錯体のX線構造解析を行い、結晶中では1個のアミン配位子のみがホウ素原子に配位した構造をとっていることがわかった。配位結合の結合距離などのその他の分子構造の特徴を明らかにすることができた。
    以上、本課題において当初の研究計画をおおむね達成することができた。今後、窒素にメチル基以外の置換基をもつもの、あるいは分子内に3個以上のアミン配位子を持つ化合物へと研究を展開していく上での基本的なデータが得られた。

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  • 安定な銅(O)錯体の合成と生成機構の解明

    Grant number:06227267  1994

    日本学術振興会  科学研究費助成事業  重点領域研究

    豊田 真司

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    Grant amount:\2000000 ( Direct Cost: \2000000 )

    反応性有機銅分子のモデルとして、分子内硫黄配位子により安定化された有機銅化合物を合成し、その構造や反応性を調べた。又、金属に配位した硫黄配位子の動的挙動についても研究を行なった。
    有機リチウム化合物とハロゲン化銅の反応から、有機銅化合物の合成を試みた。オルト(アルキルチオメチル)フェニルリチウムの反応では、有機銅化合物は得られずフェニル基が2量化したビフェニル型の化合物とそのハロゲン化銅錯体が得られた。当初、このハロゲン化銅錯体は銅(O)錯体であると考えられていたが、本課題申請後銅(I)錯体であることが判明した。X線構造解析と分子量測定から、この錯体は結晶中では高分子構造、溶液中では単量体で存在することが明らかになった。
    オルト(アルキルチオ)フェニルリチウムの反応の場合、非常に安定な有機銅化合物がハロゲン化リチウムの塩として単離できた。硫黄配位子の位置が分子の安定性を支配する重要な要因であることが示された。この安定有機銅化合物の反応性(熱分解、求電子剤との反応など)を調べた。分子内硫黄配位子の導入により反応性が低下したものの、有機銅化合物に典型的な反応性を示すことがわかった。
    銅族金属である金のスルフィド錯体における硫黄の反転過程を動的NMR法を用いて測定した。活性化パラメーターの特徴から、反転が金属-硫黄の結合解離を伴わない機構で進行することが示された。また、反転障壁に対する溶媒や金属の酸化状態の効果も明らかになった。銅や銀の錯体に同様の研究を展開していくための、基礎的な成果が得られた。

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  • 有機金属化合物(特に有機ホウ素化合物)における結合解離の動的NMR法による研究

    Grant number:01740320  1989

    日本学術振興会  科学研究費助成事業  奨励研究(A)

    豊田 真司

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    Grant amount:\900000 ( Direct Cost: \900000 )

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  • Conformational Isomerism of Acetylene Molecules

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    Grant type:Competitive

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  • Chiroptical Properties of Chiral Rotamers

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    Grant type:Competitive

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