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The fluorescence mechanism of a probe based on benzothiazole group to detect HClO

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Abstract

The hypochlorite (hypochlorite acid) produced in biological chlorine ions can resist various pathogens in the innate immune system, so it is important to design and detect the concentration of hypochlorite acid in the biological system. 2-(Benzo[d]thiazol-2-yl)-4- (methylthio) phenol (BTMSP), a fluorescent probe with large Stokes shifts, has been proposed a ESIPT-ICT dual mechanism in the experiment. But after the reaction, a new compound, BTMTP, does not have excited state intramolecular proton transfer (ESIPT) and intramolecular charge transfer (ICT) characters. In order to study the mechanism of the fluorescence probe BTMSP in detail, we have performed density functional theory (DFT) and time-dependent density functional theory (TDDFT) calculation. By computing, in the ground state, the BTMSP has the ICT process, and the BTMTP molecules are able to undergo intramolecular proton transfer reactions. The frontier molecular orbital (FMO) calculations show that the BTMSP has a large Stokes shift by ICT reaction and ESIPT coupling leading to the fluorescence emission red-shift. Although BTMTP does not have ICT character, it can undergo ESIPT reaction, causing Stokes shift decreasing.

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Acknowledgements

This work was supported by Basis Research Project of Department of Education of Liaoning Province (Grant J2019020), the Open Project of SKLMRD (the open fund of the state key laboratory of molecular reaction dynamics in DICP, CAS) and the General Program from Education department of Liaoning Province (Grant LJKZ0534).

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  1. Meng Dai, Peng Zhang: These authors contributed equally.

Authors and Affiliations

  1. School of Biological Engineering, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Meng Dai, Peng Zhang, Xiumin Liu, Yi Wang & Jing Tian

  2. School of Mechanical Engineering and Automation, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Peng Zhang

  3. Institute of Molecular Sciences and Engineering, Institute of Frontier and Interdisciplinary Science, Shandong University, Qingdao, 266237, People’s Republic of China

    Zhe Tang

  4. Lab Analyst of Network Information Center, Dalian Polytechnic University, Dalian, 116034, People’s Republic of China

    Xu Fei

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  1. Meng Dai
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Dai, M., Zhang, P., Tang, Z. et al. The fluorescence mechanism of a probe based on benzothiazole group to detect HClO. Theor Chem Acc 141, 57 (2022). https://doi.org/10.1007/s00214-022-02919-0

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