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

Abstract

A series of 5-N-arylaminothiazoles were synthesized with facile diversity-oriented synthesis from readily available starting materials via the reaction of thioamide dianions and thioformamides. The introduction of various substituents at the 2-position of a thiazole ring (i.e., 2-pyridyl, 4-methylpyridyl, and phenyl groups) and on the nitrogen atom (i.e., p-tolyl and phenyl groups) significantly influenced the absorption and emission spectra of the isolated compounds. X-ray analysis confirmed that the substituents at the amino site were twisted from a thiazole ring, while the formation of its nickel complex showed dinuclear metal complexes bridged with chlorine atoms. Moreover, the formation of zinc-thiazole complexes showed enhanced emission properties in solution and noticeable emission in a solid state. In addition, thiazole-bridged dypyrromethene type ligands showed high selectivity toward Zn+2, which make them good candidates for zinc sensing.