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Excited-State Intramolecular Proton Transfer Reaction of 3-Hydroxyflavone

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Abstract

The excited-state intramolecular proton transfer (ESIPT) reaction of 3-hydroxyflavone (3-HF) in methylcyclohexane solvent has been investigated by using the DFT and TD-DFT methods. The geometric structure, IR vibrational spectra, frontier molecular orbitals, natural bond orbital, and potential energy curves in the ground state (S0) and first excited state (S1) are analyzed to reveal the mechanism of proton transfer. The results demonstrate that there are enol- and keto- two isomers for 3-HF in the S1, which is accorded with the experimental double fluorescence bands. The 3-HF-enol can be isomerized into 3-HF-keto via ESIPT. The mechanism of proton transfer is attributed to the strengthening of hydrogen bond originated from intramolecular charge transfer. The potential energy curves in the S0 and S1 states also illuminate the tautomerism mechanism between 3-HF-enol and 3-HF-keto, and the ground-state 3-HF-keto might not exist long and is isomerized mostly into the 3-HF-enol due to its high energy or instability. This is the reason that only one absorption peak is observed for 3-HF in experiment.

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Acknowledgments

This work was partly supported by the National Natural Science Foundation of China (Grant No. 21203012), Liaoning Excellent Talents Programand (LJQ2013118), and the Foundation of State Key Laboratory of Explosion Science and Technology of Beijing Institute of Technology (KFJJ14-08M).

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Authors and Affiliations

  1. Academy of Mathematics and Physics, Department of Physics, Bohai University, Jinzhou, 121013, China

    Yanxue Jiang & Yajing Peng

  2. State Key Lab of Molecular Reaction Dynamics, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    Yajing Peng

  3. State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing, 100081, China

    Yajing Peng

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  1. Yanxue Jiang
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Correspondence to Yajing Peng.

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Jiang, Y., Peng, Y. Excited-State Intramolecular Proton Transfer Reaction of 3-Hydroxyflavone. J Clust Sci 26, 1983–1992 (2015). https://doi.org/10.1007/s10876-015-0893-7

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  • DOI: https://doi.org/10.1007/s10876-015-0893-7

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