Synthesis, Photophysical, and (Spectro)Electrochemical Properties of New Benzo[1,2-c][1,2,5]thiadiazoles and Benzo[1,2-d][1,2,3]triazoles Fused with Two Thiazole Rings

Abstract

Acylation of benzo[c][1,2,5]thiadiazole-4,7-diamine and 2-hexyl-2H-benzo[d][1,2,3]triazole-4,7-diamine with aromatic acid halides furnished the corresponding N,N′-diamides, which were converted into N,N′-dithioamides by reacting with Lawesson’s reagent. A method was developed for the preparation of previously unknown fused systems, dithiazolobenzo[1,2-c][1,2,5]thiadiazoles and dithiazolobenzo[1,2-d][1,2,3]triazoles, by oxidative photochemical cyclization of N,N′-dithioamides. The photophysical and (spectro)electrochemical properties of the obtained compounds and their polymer films electrochemically deposited on ITO were studied. The optical contrast and response time of the synthesized oligomers were determined. The results obtained allow us to consider these substances as promising candidates for electrochromic devices.