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

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• 作者：Yao Lu (1)
  Yulong Gong (1)
  Huiying Ma (1)
  Zhenqiang Wang (1)
  Haili Li (1)
  Ziping Luo (1)
  Hongru Li (1)
  Fang Gao (1)
  
• 关键词：Benzotriazole derivative ; Synthesis ; Excited state intramolecular proton transfer (ESIPT) ; Spectroscopy ; Stokes shifts ; Molecular geometry optimization
• 刊名：Chinese Science Bulletin
• 出版年：2014
• 出版时间：December 2014
• 年：2014
• 卷：59
• 期：34
• 页码：4741-4751
• 全文大小：919 KB
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• 作者单位：Yao Lu (1)
  Yulong Gong (1)
  Huiying Ma (1)
  Zhenqiang Wang (1)
  Haili Li (1)
  Ziping Luo (1)
  Hongru Li (1)
  Fang Gao (1)
  
  1. School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400044, China
  
• ISSN：1861-9541

文摘

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 260-00?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.