The synthesis, X-ray crystal structure and optical properties of novel 5-aryl-1-arylthiazolyl-3-ferrocenyl-pyrazoline derivatives

A series of novel 5-aryl-1-arylthiazolyl-3-ferrocenyl-pyrazoline derivatives has been synthesized by the reaction of ferrocenyl chalcone and thiosemicarbazide followed by the reaction with 2-bromo-1-arylethanone in 48-90% yields. The compounds were characterized using IR, (1)H NMR and HRMS and X-ray diffraction analysis. The absorption and fluorescence characteristics of the compounds were investigated in dichloromethane, chloroform and tetrahydrofuran. The results showed that the absorption maxima of the compounds vary from 316 to 347 nm depending on the group bonded to phenylthiazole rings. The electron-donating methoxyl group in phenylthiazole moiety caused red shifts in dichloromethane solution, and the electron-withdrawing chloro group resulted in blue shifts. The absorption maxima of these compounds in tetrahydrofuran were red shift compared with that in dichloromethane and chloroform. The maximum emission spectra of compounds in tetrahydrofuran were also red shift compared with that in dichloromethane. (C) 2010 Elsevier B.V. All rights reserved.