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

Anastasia S. Kostyuchenko, Evgenii B. Uliankin, Anton J. Stasyuk, Анна Л. Самсоненко, Tatyana Yu. Zheleznova, Антон Л. Шацаускас, Alexander S. Fisyuk

2022The Journal of Organic Chemistry13 citationsDOI

Abstract

This article focuses on the development of practical approaches to the preparation of benzo[1,2-d:4,3-d′]bis(thiazoles) using blue light-induced photochemical cyclization of N,N′-(1,4-aryl)dithioamides in the presence of p-chloranil as a mild oxidant. The proposed method allows to obtain benzo[1,2-d:4,3-d′]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-d:4,3-d′]bis(thiazole) and -benzo[1,2-d:4,5-d′]bis(thiazole) are studied in detail. The properties of the synthesized compounds suggest their potential applications for organic electronics.

Topics & Concepts

ChemistryThiazoleElectrochemistryChloranilPhotochemistryConjugated systemArylCombinatorial chemistryStereochemistryOrganic chemistryPhysical chemistryPolymerElectrodeAlkylOrganic Chemistry Cycloaddition ReactionsPhotochromic and Fluorescence ChemistrySulfur-Based Synthesis Techniques
Photochemical Synthesis and Electrochemical and Photophysical Properties of 2,7-Diarylbenzo[1,2-d:4,3-d′]bis(thiazoles) | Litcius