A novel solid-state photochromic compound containing double heterocycles

作者：Liu Lang^*; Sun Hubin; Abdurehman Samat; Jia Dianzeng; Guo Jixi; Wu Dongling

来源：Journal of Photochemistry and Photobiology A: Chemistry , 2013, 267: 55-59.

DOI：10.1016/j.jphotochem.2013.06.021

• Photochromism
• Pyrazolone
• Thiophene
• Proton transfer

A new compound containing double heterocycles of pyrazole and thiophene, i.e. 1,3-diphenyl-4-(2-thienylmethylene)-5-hydroxypyrazole 4-phenylsemicarbazone (1), was synthesized and characterized by elemental analysis, MS, IR, (HNMR)-H-1, (CNMR)-C-13 and X-ray single crystal diffraction. In solid state, it exhibits good photochromic properties under the UV and visible light irradiation. Upon the irradiation of UV light, the keto isomer (II) shows three IR absorption bands at 1697, 3302, 3404 cm(-1), which are not observed for the enol isomer. To understand the IR spectral changes, theoretical calculations were carried out using Gaussian 03 program. Based on analysis of the single crystal structure and the results of theoretical calculation, the photochromic mechanism is due to the double-proton transfer by intramolecular and intermolecular hydrogen bonds, leading to the isomerization between the enol and the keto form.

• 出版日期2013-9-1
• 单位中国科学院长春应用化学研究所; 新疆大学