中国物理B ›› 2022, Vol. 31 ›› Issue (3): 38201-038201.doi: 10.1088/1674-1056/ac29ad

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Influence of intramolecular hydrogen bond formation sites on fluorescence mechanism

Hong-Bin Zhan(战鸿彬)1, Heng-Wei Zhang(张恒炜)1, Jun-Jie Jiang(江俊杰)1, Yi Wang(王一)1,†, Xu Fei(费旭)2, and Jing Tian(田晶)1   

  1. 1 School of Biological Engineering, Dalian Polytechnic University, Dalian 116034, China;
    2 Laboratory Analyst of Network Information Center, Dalian Polytechnic University, Dalian 116034, China
  • 收稿日期:2021-07-23 修回日期:2021-08-22 接受日期:2021-09-24 出版日期:2022-02-22 发布日期:2022-02-24
  • 通讯作者: Yi Wang E-mail:wangyi@dlpu.edu.cn
  • 基金资助:
    Project supported by the Open Project of State Key Laboratory of Molecular Reaction Dynamics in Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences.

Influence of intramolecular hydrogen bond formation sites on fluorescence mechanism

Hong-Bin Zhan(战鸿彬)1, Heng-Wei Zhang(张恒炜)1, Jun-Jie Jiang(江俊杰)1, Yi Wang(王一)1,†, Xu Fei(费旭)2, and Jing Tian(田晶)1   

  1. 1 School of Biological Engineering, Dalian Polytechnic University, Dalian 116034, China;
    2 Laboratory Analyst of Network Information Center, Dalian Polytechnic University, Dalian 116034, China
  • Received:2021-07-23 Revised:2021-08-22 Accepted:2021-09-24 Online:2022-02-22 Published:2022-02-24
  • Contact: Yi Wang E-mail:wangyi@dlpu.edu.cn
  • Supported by:
    Project supported by the Open Project of State Key Laboratory of Molecular Reaction Dynamics in Dalian Institute of Chemical Physics (DICP), Chinese Academy of Sciences.

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摘要： The fluorescence mechanism of HBT-HBZ is investigated in this work. A fluorescent probe is used to detect HClO content in living cells and tap water, and its structure after oxidation by HClO (HBT-ClO) is discussed based on the density functional theory (DFT) and time-dependent density functional theory (TDDFT). At the same time, the influence of the probe conformation and the proton transfer site within the excited state molecule on the fluorescence mechanism are revealed. Combined with infrared vibrational spectra and atoms-in-molecules theory, the strength of intramolecular hydrogen bonds in HBT-HBZ and HBT-ClO and their isomers are demonstrated qualitatively. The relationship between the strength of intramolecular hydrogen bonds and dipole moments is discussed. The potential energy curves demonstrate the feasibility of intramolecular proton transfer. The weak fluorescence phenomenon of HBT-HBZ in solution is quantitatively explained by analyzing the frontier molecular orbital and hole electron caused by charge separation. Moreover, when strong cyan fluorescence occurs in solution, the corresponding molecular structure should be HBT-ClO(T). The influence of the intramolecular hydrogen bond formation site on the molecule as a whole is also investigated by electrostatic potential analysis.

关键词: benzothiazole, excited state intramolecular proton transfer, fluorescence mechanism, density functional theory

Abstract: The fluorescence mechanism of HBT-HBZ is investigated in this work. A fluorescent probe is used to detect HClO content in living cells and tap water, and its structure after oxidation by HClO (HBT-ClO) is discussed based on the density functional theory (DFT) and time-dependent density functional theory (TDDFT). At the same time, the influence of the probe conformation and the proton transfer site within the excited state molecule on the fluorescence mechanism are revealed. Combined with infrared vibrational spectra and atoms-in-molecules theory, the strength of intramolecular hydrogen bonds in HBT-HBZ and HBT-ClO and their isomers are demonstrated qualitatively. The relationship between the strength of intramolecular hydrogen bonds and dipole moments is discussed. The potential energy curves demonstrate the feasibility of intramolecular proton transfer. The weak fluorescence phenomenon of HBT-HBZ in solution is quantitatively explained by analyzing the frontier molecular orbital and hole electron caused by charge separation. Moreover, when strong cyan fluorescence occurs in solution, the corresponding molecular structure should be HBT-ClO(T). The influence of the intramolecular hydrogen bond formation site on the molecule as a whole is also investigated by electrostatic potential analysis.

Key words: benzothiazole, excited state intramolecular proton transfer, fluorescence mechanism, density functional theory

中图分类号:  (Charge (electron, proton) transfer in biological systems)

  • 82.39.Jn
31.15.ee (Time-dependent density functional theory) 87.15.A- (Theory, modeling, and computer simulation)