Theoretical Investigation of Photochromic Reactions of 6-Hydroxy-5,12-naphthacenequinone and Its Derivatives Bearing Methyl or Phenyl Groups
YIN Jing-Hua1; LIAN Hui-Qin1; ZHOU Zi-Yan2; ZHAO Ji-Yang1; WU Xue*,1
(1 Key Laboratory of Natural Resources of the Chanbai Mountain and Functional Molecules, Ministry of Education, Yanji 133002)
(2 College of Chemical Engineering, Shandong University of Technology, Zibo 255049)
Photoisomerizations of 6-hydroxy-5,12-naphthacenequinone and its derivatives bearing methyl and phenyl group were theoretically investigated with density functional theory method and ab initio CIS method at the B3LYP 6-31G basis set, respectively. The obtained potential energy curves disclosed that a four-state cycle existed in the ground and excited states. It was also found that the activation energy for the methyl transfer was higher compared to the phenyl transfer, which was consistent to the experimental results that the photoisomerization of the phenyl substituted derivative was more rapid than the methyl substituted derivatives. Further hybrid time-dependent density functional theory (TD-DFT) was used to investigate the absorption and fluorescence spectra of these compounds under solvent effect condition. The calculated values were in agreement with the experimental results and the excitation condition of photochromic reactions.