Modular synthesis of 1H-indenes, dihydro-s-indacene, and diindenoindacene--a carbon-bridged p-phenylenevinylene congener

Xiaozhang Zhu; Chikahiko Mitsui; Hayato Tsuji; Eiichi Nakamura

doi:10.1021/ja905626b

Modular synthesis of 1H-indenes, dihydro-s-indacene, and diindenoindacene--a carbon-bridged p-phenylenevinylene congener

J Am Chem Soc. 2009 Sep 30;131(38):13596-7. doi: 10.1021/ja905626b.

Authors

Xiaozhang Zhu¹, Chikahiko Mitsui, Hayato Tsuji, Eiichi Nakamura

Affiliation

¹ Department of Chemistry, School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 19728709
DOI: 10.1021/ja905626b

Abstract

A variety of 1H-indenes, dihydro-s-indacenes, and diindenoindacenes, carbon-bridged phenylenevinylene derivatives, can be synthesized in good to high yields using as a synthetic module a 3-lithioindene compound made available by reductive cyclization of an alkynylbenzene derivative. The planar analogues of oligophenylenevinylene compounds thus synthesized show physical properties beneficial for use as ambipolar organic semiconductor materials.