Photochemical Synthesis and Electrochemical and Photophysical Properties of 2,7-Diarylbenzo[1,2-d:4,3-d′]bis(thiazoles)

Abstract

This article focuses on the development of practical approaches to the preparation of benzo[1,2-<i>d</i>:4,3-<i>d</i>']bis(thiazoles) using blue light-induced photochemical cyclization of <i>N,N</i>'-(1,4-aryl)dithioamides in the presence of <i>p</i>-chloranil as a mild oxidant. The proposed method allows to obtain benzo[1,2-<i>d</i>:4,3-<i>d</i>']bis(thiazoles) containing donor substituents in the conjugated chain. Photophysical and (spectro)electrochemical properties of 2,6-di([2,2'-bithiophen]-5-yl)benzo[1,2-<i>d</i>:4,3-<i>d'</i>]bis(thiazole) and -benzo[1,2-<i>d</i>:4,5-<i>d</i>']bis(thiazole) are studied in detail. The properties of the synthesized compounds suggest their potential applications for organic electronics.