Synthesis of Tetra(3-thienyl)biphenoquinone and its Charge Transfer Complex with Perylene

Ryotaro Fujii, Md Awlad Hossain, Hisato Akimoto, Kazunori Hirabayashi, Toshio Shimizu, Kazuhiko Akiyama, Kenta Goto, Hiroyuki Nishikawa, Ken Ichi Yamashita, Ken Ichi Sugiura

Research output: Contribution to journalArticle

Abstract

Tetra(thienyl)biphenoquinones were designed and synthesized. An oxidative coupling of 2,6-bis(3-thienyl)phenol with PbO2 in acetic acid afforded the corresponding biphenoquinone along with 2,6-bis(3-thienyl)-p-benzoquinone. This biphenoquinone showed properties characteristic of a π-expanded quinone, that is, positively shifted reduction potential and light absorption in the visible region. In contrast to kinetically protected biphenoquinones with bulky substituents at the ortho-positions of carbonyls, the title compounds take a planar structure because of the small steric repulsion of the five-membered thiophene rings. Its charge transfer complex with perylene is characterized by a well-overlapped mixed stack.

Original languageEnglish
Pages (from-to)171-178
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume7
Issue number1
DOIs
Publication statusPublished - Jan 2018

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Fujii, R., Hossain, M. A., Akimoto, H., Hirabayashi, K., Shimizu, T., Akiyama, K., Goto, K., Nishikawa, H., Yamashita, K. I., & Sugiura, K. I. (2018). Synthesis of Tetra(3-thienyl)biphenoquinone and its Charge Transfer Complex with Perylene. Asian Journal of Organic Chemistry, 7(1), 171-178. https://doi.org/10.1002/ajoc.201700560