Theoretical Study of Excited State Proton Transfer of 2-Phenyl- benzotriazole Derivatives with Different Proton Donor
YI Ping-Gui, ZHOU Ji-Ming, WANG Chao-Xu, YU Xian-Yong, LI Xiao-Fang, CHEN Jian, LIU Zheng-Jun
(Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201)
Abstract：A theoretical study of excited state intramolecular proton transfer (ESIPT) and the photophysical mechanism of UV absorbers of 2-phenylbenzotriazole derivatives with different proton donor: 2-(2-hydroxyphenyl)benzotriazole (H-TIN), 2-(2-aminophenyl)benzotriazole (APyBT) and 2-(2-Mercaptophenyl)benzotriazole (MPyBT) have been performed by density functional theory (DFT) and second order Møller-Plesset perturbation theory (MP2). The results show that the most stable tautomer is normal configuration N which has intramolecular hydrogen bond for different tautomers of three compounds in ground state, while the tautomer T and twisted configuration Ttwisted are unstable in ground state. The potential energy curves for ESIPT of three compounds show that H-TIN and APyBT can occurs ESIPT that overcome the energy barrier of ca. 7.06 and 20.7 kJ/mol, respectively, however the ESIPT of MPyBT can occur without a barrier|meanwhile combined the results of molecular orbital and charge difference density three-dimensional cube for the three compounds, it indicates that H-TIN, APyBT and MPyBT can occur the fast ESIPT and twisted intramolecular charge transfer, these reasons show that they all have good UV stabilization.
易平贵, 周继明, 汪朝旭, 于贤勇, 李筱芳, 陈建, 刘峥军. 含不同质子供体的2-苯基苯并三唑衍生物激发态质子转移的理论研究[J]. 化学学报, 2011, 69(14): 1645-1653.
YI Ping-Gui, ZHOU Ji-Ming, WANG Chao-Xu, YU Xian-Yong, LI Xiao-Fang, CHEN Jian, LIU Zheng-Jun. Theoretical Study of Excited State Proton Transfer of 2-Phenyl- benzotriazole Derivatives with Different Proton Donor. Acta Chimica Sinica, 2011, 69(14): 1645-1653.