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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 185, 2010 - Issue 5-6: A Tribute to the Chemistry of Professor Naomichi Furukawa
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Original Articles

Synthesis and Properties of Thienylene-Ethynylene-Tetrathiafulvalene Oligomers

Masashi Hasegawa Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo, Japan
,
Kenji Hara Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo, Japan
,
Ken-ichi Tokuyama Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo, Japan
&
Masahiko Iyoda Department of Chemistry, Graduate School of Science and Engineering, Tokyo Metropolitan University, Hachioji, Tokyo, Japan
Pages 1061-1067 | Received 02 Dec 2008, Accepted 28 Dec 2008, Published online: 27 May 2010
 
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Abstract

A series of thienylene-ethynylene-tetrathiafulvalene oligomers 1–6 have been synthesized by the Sonogashira reaction of iodo-tetrathiafulvalene derivatives with thienylethynes. The X-ray structure of 4,5-bis(2-thienylethynyl)tetrathiafulvalene (1b) revealed a planar structure of the molecule. The electronic spectra of neutral oligomers 1–6 suggest a partial intramolecular charge transfer between the TTF and thienylethyne units. The cyclic voltammetric measurements of 1–4 showed multi-redox processes.

Acknowledgments

Dedicated to Professor Naomichi Furukawa on the occasion of his 70th birthday.The present affiliation for Masashi Hasegawa is Department of Chemistry, School of Science, Kitasato University, Kanagawa 228-8555, Japan.The authors are grateful to Dr. Y. Kuwatani (VSN, Inc.), Prof. H. Matsuyama (Muroran Institute of Technology), and Prof. M. Yoshida (Shimane University) for helpful discussions. This work was partly supported by a Grant-in-Aid for Science Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.

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