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Insights into the excited state hydrogen bond and proton transfer behaviors associated with solvent polarity for NHBQ fluorophore: a theoretical study

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Abstract

Inspired by the excellent photochemical properties of hydroxybenzo[h]quinoline and its derivatives, in this work, the novel electron withdrawing nitro substituted HBQ (i.e., NHBQ) fluorophore is explored about its photo-induced behaviors. By investigating the photoexcitation characteristics in different solvents, the solvent-polarity-related photo-induced hydrogen bond of NHBQ indicates polar aprotic solvents largely enhance S1-state hydrogen bond interactions. Charge reorganization stemming from photoexcitation, strengthening excited state hydrogen bond effects, and the polarity-dependent energy gap of frontier molecular orbitals further reveals the excited state intramolecular proton transfer (ESIPT) tendency. Insights into potential energy curves along ESIPT paths in solvents with different polarities, we present that solvent polarity could harness the ESIPT behavior for NHBQ compound.

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Data are available on request from the corresponding author.

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Acknowledgements

We are grateful to the General Program of the Education Department of Liaoning Province (Grant No. LJKMZ20221473), the Fundamental Research Funds for the Central Universities (Grant no. 2022MS120), and the Natural Science Research Project and Cultivation Funding for Excellent Youth Scholars of Anhui Province (Grant Nos. 2022AH051342 and gxgnfx2022030). The main part of this work was carried out at Shanxi Supercomputing Center of China, and relevant calculations were performed on TianHe-2.

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Authors and Affiliations

  1. College of Physical Science and Technology, Shenyang Normal University, Shenyang, 110034, China

    Liming Fan & Jinfeng Zhao

  2. Hebei Key Laboratory of Physics and Energy TechnologyDepartment of Mathematics and Physics, North China Electric Power University, Baoding, 071003, China

    Hao Dong

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

    Bing Jin, Jinfeng Zhao & Xiaoxiao Li

Authors
  1. Hao Dong
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  2. Bing Jin
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  3. Liming Fan
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  4. Jinfeng Zhao
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Contributions

Hao Dong: Conceptualization, Methodology, Data Analysis, Writing - Review & Editing, Validation and Supervision Bing Jin: Quantum Chemical Simulations, Methodology, Writing - Review & Editing Liming Fan: Validation and Supervision, Data Analysis and Writing - Review & Editing Jinfeng Zhao: Conceptualization, Methodology, Data Analysis and Writing - Review & Editing Xiaoxiao Li: Quantum Chemical Simulations, Methodology, Data Analysis and Writing - Review & Editing

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Correspondence to Jinfeng Zhao.

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Dong, H., Jin, B., Fan, L. et al. Insights into the excited state hydrogen bond and proton transfer behaviors associated with solvent polarity for NHBQ fluorophore: a theoretical study. Theor Chem Acc 142, 37 (2023). https://doi.org/10.1007/s00214-023-02979-w

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