4-Formyl-2-(2H-benzotriazol-2-yl)-phenol: an ESIPT chromophore  

作　　者：Yao Lu Yulong Gong Huiying Ma Zhenqiang Wang Haili Li Ziping Luo Hongru Li Fang Gao 

机构地区：[1]School of Chemistry and Chemical Engineering, Chongqing University

出　　处：《Chinese Science Bulletin》2014年第34期4741-4751,共11页

基　　金：supported by Chongqing Natural Science Foundation(CSTC2012jj B50007,CSTC2010BB0216);the National Natural Science Foundation of China(21376282);F.Gao thanks the supporting from the Program for New Century Excellent Talents(NCET-10-0876);the Fundamental Research Funds for the Central Universities(CDJZR10220006);Y.Lu thanks the Graduate Innovation Foundation of Chongqing University(CDJXS11131146)

摘　　要：In the present work, excited state intramolecular proton transfer(ESIPT) emission properties of a new benzotriazole derivative 4-formyl-2-(2H-benzotriazol-2-yl)-phenol(C1) were studied. 4-Formyl-2-(2H-benzotriazol-2-yl)-methoxy-benzene(C2), 4-formyl-2-(2H-benzotriazol-2-yl)-phenyl acetate(C3) and 4-methyl-2-(2H-benzotriazol-2-yl)-phenol(C4) were used as the reference molecules.1H NMR chemical shift of hydroxy group in C1 was located at more down field than that of C4 or p-hydroxy-benzaldehyde(C5), respectively. C1 showed two absorption bands in the range of 260–400 nm zones in various solvents, while C2 and C3 exhibited single absorption band. The equal molar mixtures of C2/C5 or C3/C5 showed single absorption band.C2 and C3 displayed single fluorescence emission band in various solvents, while C1 exhibited dual emission bands in some strong polar solvents. Furthermore, the second emission band in these strong polar solvents showed the large Stokes shift. The results show that the second emission band of C1 was produced by ESIPT. C2 and C3 could not undergo ESIPT due to no hydroxy group. The geometry optimization calculation of enol and keto forms in the ground and excited states of C1 provided tough theoretical evidences of ESIPT.In the present work, excited state intramolecular proton transfer （ESIPT） emission properties of a new benzotriazole derivative 4-formyl-2-（2H-benzotriazol-2-yl）- phenol （C1） were studied. 4-Formyl-2-（2H-benzotriazol-2- yl）-methoxy-benzene （C2）, 4-formyl-2-（2H-benzotriazol-2- yl）-phenyl acetate （C3） and 4-methyl-2-（2H-benzotriazol- 2-yl）-phenol （C4） were used as the reference molecules. ^1H NMR chemical shift of hydroxy group in C1 was located at more down field than that of C4 or p-hydroxy-benzaldehyde （C5）, respectively. C1 showed two absorption bands in the range of 260-400 nm zones in various solvents, while C2 and C3 exhibited single absorption band. The equal molar mixtures of C2/C5 or C3/C5 showed single absorption band. C2 and C3 displayed single fluorescence emission band in various solvents, while C1 exhibited dual emission bands in some strong polar solvents. Furthermore, the second emission band in these strong polar solvents showed the large Stokes shift. The results show that the second emission band of C1 was produced by ESIPT. C2 and C3 could not undergo ESIPT due to no hydroxy group. The geometry optimization calculation of enol and keto forms in the ground and excited states of C1 provided tough theoretical evidences of ESIPT.

关 键 词：苯并三唑 甲酰基 激发态分子内质子转移 苯酚 极性溶剂 生色 发射性能 三唑衍生物 

分 类 号：O626.26[理学—有机化学] TQ463[理学—化学]