Synthesis and Photophysical Properties of 5-N-Arylaminothiazoles with Sulfur-Containing Groups on the Aromatic Ring at the 2-Position

Abstract

5-Amino-2-(4-methylsulfanylphenyl)thiazoles were prepared by reacting 4-methylsulfanylbenzthioamides and N,N-diarylthioformamides. Demethylaiton of the resulting thiazoles gave 4-sulfhydrylphenylthiazoles. Starting from these thiazoles, a range of thiazoles with sulfur-containing functional groups were prepared. Oxidation of the thiazoles also gave thiazoles with sulfenyl and sulfonyl groups. The photophysical properties of a series of thiazoles were determined. The effects of sulfur-containing functional groups on the electronic structures of the thiazoles were elucidated by DFT calculations. Oxidation of the divalent sulfur atoms introduced to thiazoles helped to lower the energy levels of the LUMOs of the resulting thiazoles.

5-N-Arylaminothiazoles with pyridyl groups and their first-row transition metal complexes: synthesis, photophysical properties, and Zn sensing

“…Therefore, a considerable number of these compounds have been developed. [38][39][40][41][42][43][44] 5-N-Arylaminothiazoles are a class of uorescent compounds bearing a exible conformational geometry with non-planar carbon skeletons. 38 These compounds are synthesized by reacting secondary thioamide and thioformamides via thioamide dianions and thiazolines.…”