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Paper | Special issue | Vol 97, No. 1, 2018, pp.409-421
Published online, 13th March, 2018
DOI: 10.3987/COM-18-S(T)28
Synthesis and Photophysical Properties of 5-N-Arylaminothiazoles with Sulfur-Containing Groups on the Aromatic Ring at the 2-Position

Toshiaki Murai,* Hidenori Furukawa, and Kirara Yamaguchi

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu, Gifu 501-1193, Japan


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.