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JAPAN NANONET BULLETIN - 73rd Issue - June 22, 2006

YOUNG RESEARCHERS’ INTRODUCTION

Shigehiro YAMAGUCHI
Professor, Department of Chemistry, Graduate School of Science, Nagoya University
Researcher, Solution Oriented Research for Science and Technology (SORST), Japan Science and Technology Agency (JST)

Creation of new functional π-electron organic materials based on main group chemistry

(Issued in Japanese: September 15, 2004)

The creation of new organic π-electron materials is the central topic in research fields including organic
(opto)electronics, which involves devices such as organic electroluminescent (EL) devices and thin film transistors, and molecular-scale electronics. We have based our synthetic research on main group chemistry. Molecular design exploiting the characteristic properties of main group elements provides access to new π-electron materials with intriguing photophysical and electronic properties.

In particular, our strategy relies on the incorporation of main group elements into π-conjugated ring systems, in which the orbital interaction between the main group element and π-conjugated moiety effectively occurs. Using this approach, we have, so far, synthesized various π-electron materials with unique electronic structures. One example is a silicon-containing π-electron system, 2,5-bis(bipyridyl)silole. This molecule is an extremely efficient electron-transporting material, due to the σ*-π* conjugation in the silole ring, and has already been put into the commercial use in organic EL displays. We are currently extending this silicon chemistry to other elements and have synthesized several other types of rigid planar π-electron systems, including dibenzoborole-based π-electron compounds, silicon-bridged oligo(phenylenevinylene)s, and sulfur- or selenium-containing heteroacenes, by using newly developed efficient synthetic methodologies.

The “main group chemistry approach” will lead to new and fascinating π-electron materials that cannot be achieved by the ordinary organic chemistry. We hope to develop platform molecules for the next-generation electronic and optoelectronic applications.

Shigehiro YAMAGUCHI
Shigehiro YAMAGUCHI
Professor, Department of Chemistry, Graduate School of Science, Nagoya University,
Researcher, Solution Oriented Research for Science and Technology (SORST), Japan Science and Technology Agency (JST)
 
1993Master of Engineering, Kyoto University
1993
~2002
Assistant Professor, Institute for Chemical Research, Kyoto University
1997Doctor of Engineering, Kyoto University
2000
~2001
Visiting Scholar, Massachusetts Institute of Technology
2001
~2004
Researcher, Precursory Research for Embryonic Science and Technology (PRESTO), Japan Science and Technology Agency (JST)
2003
~2005
Associate Professor, Department of Chemistry, Graduate School of Science, Nagoya University
2004
~present
Researcher, Solution Oriented Research for Science and Technology (SORST), JST
2005
~present
Professor, Department of Chemistry, Graduate School of Science, Nagoya University
 
Award
1997Chisso Award,
Synthetic Organic Chemistry, Japan
1999Young Scientist Award, Silicon Chemical Society of Japan
2002The Chemical Society of Japan Award for Distinguished Young Chemists
2005Young Scientist Award from the Minister of Education, Culture, Sports, Science and Technology
 
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Fig.1
Fig.1
The lowest unoccupied molecular orbital (LUMO) of 2,5-bis(bipyridyl)silole and an organic electroluminescent device using this molecule as an electron-transporting material.

Fig.2
Fig.2
Highly planar silicon-bridged oligo(phenylenevinylene)s synthesized by the newly developed intramolecular reductive cyclization.

Relevant papers
  1. Yamaguchi, S., Xu, C. & Tamao, K.
    Bis-Silicon-Bridged Stilbene Homologues Synthesized by New Intramolecular Reductive Double Cyclization
    J. Am. Chem. Soc. 125, 13662-13663 (2003).
  2. Yamaguchi, S., Shirasaka, T., Akiyama, S. & Tamao, K.
    Dibenzoborole-Containing π-Electron Systems: Remarkable Fluorescence Change Based on the ON/OFF-Control of the pπ-π* Conjugation
    J. Am. Chem. Soc. 124, 8816-8817 (2002).
  3. Yamaguchi, S. & Tamao, K.
    Cross-Coupling Reactions in the Chemistry of Silole-Containing π-Conjugated Oligomers and Polymers
    J. Organomet. Chem. 653, 223-228 (2002).