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The sensing mechanism of fluorescent probe for PhSH and the process of ESIPT

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Abstract

The detection mechanism of fluorescent probe FQ-DNP (DNP: 2,4-dinitropheno) for PhSH and the detailed ESIPT process of its product 2-(6-(diethylamino) quinolin-2-yl)-3–Hydroxy-4H-chromen-4-one (FQ-OH) have been revealed by density functional theory (DFT) and time-dependent density functional theory (TD-DFT). For FQ-OH, the decreased bond length of H6–N7 and RDG analysis illustrate that the strength of hydrogen bond H6–N7 has been enlarged after photoexcitation, creating a good condition for ESIPT. To illustrate the ESIPT process in detail, the potential energy curves are performed and the transition state reaction energy is calculated. In the S0 state, the FQ-OH could happen proton transfer (PT) to form keto, but the keto form is more unstable than enol form. After photoexcitation, in the S1 state, FQ-OH could happen PT to produce stable keto form. Excited dynamic simulation shows that PT happens at 71.5 fs. The calculated absorption and emission spectra are in agreement with the experimental data, and the calculated Stokes shift is 160 nm. Frontier molecular orbitals (FMOs) and hole–electron analysis show that twisted intramolecular charge transfer (TICT) is responsible for the fluorescent quenching of FQ-DNP.

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Acknowledgements

This work was supported by the Science and Technology Basic Resources Investigation Program of China (No. 2019FY100500), 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. Hengwei Zhang and Ke Zhang have contributed equally to this work.

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

    Hengwei Zhang, Jiarui Liu, Yi Wang & Fang Yu

  2. Institute of Applied Ecology, Chinese Academy of Sciences, Shenyang, 110016, People’s Republic of China

    Ke Zhang

  3. University of Chinese Academy of Sciences, Beijing, 100049, People’s Republic of China

    Ke Zhang

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Zhang, H., Zhang, K., Liu, J. et al. The sensing mechanism of fluorescent probe for PhSH and the process of ESIPT. Photochem Photobiol Sci 21, 1055–1065 (2022). https://doi.org/10.1007/s43630-022-00193-4

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