Faculty Profiles - YAMAGUCHI, Shigehiro

Papers - YAMAGUCHI, Shigehiro

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Coordination-Induced Intramolecular Double Cyclization: Synthesis of Boron-Bridged Dipyridylvinylenes and Dithiazolylvinylenes

Qiang Zhao, Hongyu Zhang, Atsushi Wakamiya, Shigehiro Yamaguchi

SYNTHESIS-STUTTGART ( 1 ) page： 127 - 132 2009.1

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：GEORG THIEME VERLAG KG

Di(heteroaryl)acetylenes having a pyridyl or thiazolyl as the heteroaryl group underwent a reaction with bromodibenzoborole to produce coordination complexes, which were further treated with water to promote the intramolecular cascade double cyclization to produce the dibenzoborolyl-bridged ladder di(heteroaryl)vinylenes. For the thiazolyl derivative, further derivatization at the terminal positions produced a bis(dimesitylboryl)-substituted derivative. The ladder molecules prepared showed ail intense emission in the fluorescence spectra as well as reversible reduction waves at low reduction potentials in the cyclic voltammetry.

DOI： 10.1055/s-0028-1083271

Web of Science

FT Raman and DFT Study on a Series of All-anti Oligothienoacenes End-Capped with Triisopropypsilyl Groups

R. M. Osuna, V. Hernández, J. T. L. Navarrete, J. Aragó, P. M. Viruela, E. Ortí, Y. Suzuki, S. Yamaguchi, J. T. Senssler, A. J. Matzger

ChemPhysChem. Vol. 10 page： 3069-3076 2009

Coordination-Induced Intramolecular Double Cyclization: Synthesis of Boron-Bridged Dipyridylvinylenes and Dithiazolylvinylenes

Q. Zhao, H. Zhang, A. Wakamiya, and S. Yamaguchi

Synthesis, 40th special issue page： 127-132 2009

Electronic Structure of Bis(benzo)pentathienoacene in Gas and Solid Phase: Ultraviolet Photoemission Spectroscopy and Energy Band Calculation

H. Yoshida, Y. Watazu, N. Sato, T. Okamoto, and S. Yamaguchi

Appl. Phys. A Vol. 95 page： 185-191 2009

*Intense Solid-State Blue Emission with a Small Stokes' Shift: pi-Stacking Protection of Diphenylanthracene Skeleton

A. Iida and S. Yamaguchi

Chem. Commun. page： 3002-3004 2009

5-Aryl-3,3,4,4-tetramethyl-3,4-dihydro-3H-pyrrol-2-imines

S. Janich, R. Froehlich, A. Wilken, J. von Zamory, A. Wakamiya, S. Yamaguchi, and E.-U. Wuerthwein

Eur. J. Org. Chem. page： 2077-2087 2009

Structural Modification of Silicon-Bridged Ladder Stilbene Oligomers and Distyrylbenzenes

H. Yamada, C. Xu, A. Fukazawa, A. Wakamiya, and S. Yamaguchi

Macro. Chem. Phys. Vol. 210 page： 904-916 2009

Long-Lived Exciplex Formation and Delayed Excition Emission in Bulk Heterojunction Blends of Silole Derivative and Polyfluorene Copolymer: The Role of Morphology on Exciplex Formation and Charge Separation

J. J. Benson-Smith, J. Wilson, C. Dyer-Smith, K. Mouri, S. Yamaguchi, H. Murata, and J. Nelson

J. Phys. Chem. B, Vol. 113 page： 7794-7799 2009

Intramolecular Reductive Double Cyclization of o,o'-Bis(arylcarbonyl)diphenylacetylenes: Synthesis of Ladder π-Conjugated Skeletons

H. Zhang, T. Karasawa, H. Yamada, A. Wakamiya, and S. Yamaguchi

Org. Lett. Vol. 11 page： 3076-3079 2009

Tetraaryl-tetradecahydroporphyrazins: Novel Porphyrin Derivatives Featuring a Cyclic Benzene Ring Tetramer

S. Janich, R. Froehlich, A. Wakamiya, S. Yamaguchi, and E.-U. Wuerthwein

Chem. Eur. J. Vol. 15 page： 10457-10463 2009

Highly Emissive Diborylphenylene-Containing Bis(phenylethynyl)benzenes: Structure–Photophysical Property Correlations and Fluoride Ion Sen

C.-H. Zhao, E. Sakuda, A. Wakamiya, and S. Yamaguchi

Chem. Eur. J. Vol. 15 page： 10603-10612 2009

*A B-B Bond-Containing Polycyclic π-Electron System: Dithieno-1,2-dihydro-1,2-diborin and Its Dianion Reviewed

A. Wakamiya, K. Mori, T. Araki, and S. Yamaguchi

J. Am. Chem. Soc. Vol. 131 page： 10850-10851 2009

Ladder pi-Conjugated Materials Containing Main Group Elements

A. Fukazawa, S. Yamaguchi

Chem. Asian J. Vol. 4 page： 1386-1400 2009

Oxidation of End-Capped Pentathienoacenes and Characterization of Their Radical Cations

R. M. Osuna, M. C. R. Delgado, V. V. Hernández, J. T. L. Navarrete, B. Vercelli, G. Zotti, J. J. Novoa, Y. Suzuki, S. Yamaguchi, J. T. Henssler, A. J. Matzger

Chem. Eur. J Vol. 15 page： 12346-12361 2009

Benzo[b]phosphole-Containing π-Electron Systems: Synthesis Based on an Intramolecular trans-Halophosphanylation and Some Insights into Their Properties

A. Fukazawa, Y. Ichihashi, Y. Kosaka, and S. Yamaguchi

Chem. Asian J. Vol. 4 page： 1729-1740 2009

Regioselective Unsymmetrical Tetraallylation of C60 through Palladium Catalysis

M. Nambo, A. Wakamiya, S. Yamaguchi, and K. Itami

J. Am. Chem. Soc. Vol. 131 page： 15112-15113 2009

Intense solid-state blue emission with a small Stokes' shift: pi-stacking protection of the diphenylanthracene skeleton

Azusa Iida, Shigehiro Yamaguchi

CHEMICAL COMMUNICATIONS ( 21 ) page： 3002 - 3004 2009

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：ROYAL SOC CHEMISTRY

Intense blue emissions with a small Stokes' shift both in solution and in the solid state were attained by introducing (pentafluorophenyl) dimethylsilyl groups to a 9,10-diphenylanthracene skeleton as the pi-stacking tethers.

DOI： 10.1039/b901794a

Web of Science

PubMed

Benzo[b]phosphole-Containing pi-Electron Systems: Synthesis Based on an Intramolecular trans-Halophosphanylation and Some Insights into Their Properties

Aiko Fukazawa, Yasunori Ichihashi, Youhei Kosaka, Shigehiro Yamaguchi

CHEMISTRY-AN ASIAN JOURNAL Vol. 4 ( 11 ) page： 1729 - 1740 2009

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

The intramolecular trans-halophosphanylation of 2-(aminophosphanyl)phenylacetylenes mediated by PBr3 followed by the oxidation with H2O2 produces 3-bromobenzo[b]phosphole oxide derivatives. This cyclization is also used for the synthesis of a 3-iodo derivative by conducting the reaction in the presence of LiI. Based on this synthetic method, various benzophosphole-containing pi-conjugated compounds, including a phosphoryl and methylene-bridged stilbene 10, 2,3,6,7-tetraphenylbenzo[1,2-b:4,5-b']diphosphole-P,P'-dioxides 11, and their phosphine sulfide derivatives 12, are synthesized. The study of the structure-property relationships in a series of the bridged stilbenes, including a bis(methylene)-bridged stilbene 10, and a bis-(phosphoryl)-bridged stilbene, reveals that as the contribution of the phosphoryl groups increased, the absorption and emission maxima substantially shift to longer wavelengths. The intrinsic substituent effects of the phosphoryl group in this skeleton are to decrease the oscillator strength of the electronic transition and thus decrease the radiative decay rate constants from the singlet excited state. Nevertheless, these compounds maintain high fluorescence quantum yields (Phi(F) > 0.8) owing to the significantly retarded non-radiative decay process. In the study of the benzodiphosphole derivatives 11 and 12, their cyclic voltammetry revealed that both of the phosphoryl and phosphine sulfide derivatives have low reduction potentials (-1.7 to -1.8 V vs ferrocene/ferrocenium couple) with the high reversibility of the redox waves. These compounds also showed high thermal stabilities with the high glass transition temperatures of 147-159 degrees C, indicative of their potential utilities as amorphous materials.

DOI： 10.1002/asia.200900303

Web of Science

PubMed

5-Aryl-3,3,4,4-tetramethyl-3,4-dihydro-3H-pyrrol-2-imines

S. Janich, R. Froehlich, A. Wilken, J. von Zamory, A. Wakamiya, S. Yamaguchi, E.-U. Wuerthwein

Eur. J. Org. Chem. page： 2077-2087 2009

Highly Emissive Diborylphenylene-Containing Bis(phenylethynyl)benzenes: Structure-Photophysical Property Correlations and Fluoride Ion Sensing

Cui-Hua Zhao, Eri Sakuda, Atsushi Wakamiya, Shigehiro Yamaguchi

CHEMISTRY-A EUROPEAN JOURNAL Vol. 15 ( 40 ) page： 10603 - 10612 2009

Language：Japanese Publishing type：Research paper (scientific journal) Publisher：WILEY-V C H VERLAG GMBH

A series of 2,5-bis(dimesitylboryl)-1,4-bis(arylethynyl)benzenes 1-6 that contain various p-substituents on the terminal benzene rings, including NPh2 (1), OMe (2), Me (3), H (4), CF3 (5), and CN (6) groups, were synthesized, and the effects of the p-substituents on the absorption and fluorescence properties were investigated both in solution and in the solid state. Linear relationships were obtained not only between the Hammett sigma(+)(p) constants of the p-substituents and the absorption and fluorescence maxima, quantum yields, and excited-state dynamics parameters in solution, but also between the sigma(+)(p) constants and the fluorescence quantum yields in the solid state. An important finding extracted from these results is that the suppressed fluorescence quenching in the solid state is a common feature for the present laterally boryl-substituted pi-conjugated skeletons. Hence, the diborylphenylene can serve as a useful core unit to develop highly emissive organic solids. In fact, most of the derivatives showed more intense emission in the solid state than in solution. In addition to these studies, the titration experiment of 1 by the addition of nBu(4)NF was conducted, which showed the stepwise bindings of two fluoride ions with high association constants as well as a drastic change in the fluorescence spectra, while constantly maintaining high quantum yields (0.61-0.76), irrespective of the binding modes. This result also demonstrated the potential utility of the present molecules as an efficient fluorescent fluoride ion sensor.

DOI： 10.1002/chem.200900864

Web of Science

PubMed

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Papers - YAMAGUCHI, Shigehiro