Modular Synthesis of 1H-Indenes, Dihydro-s-Indacene, and Diindenoindacene-a Carbon-Bridged p-Phenylenevinylene Congener

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.