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Theoretical Investigation of the ESIPT Mechanism for the 1-Hydroxy-9H-fluoren-9-one and 1-Hydroxy-11H-benzo[b]fluoren-11-one Chromophores

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Abstract

The excited state intramolecular proton transfer (ESIPT) dynamics of the 1-hydroxy-9H-fluoren-9-one (HHF) and 1-hydroxy-11H-benzo[b]fluoren-11-one (HHBF) chromophores were investigated theoretically. The calculated bond lengths and angles, hydrogen bond energies and infrared vibrational spectra involved in the hydrogen bonding of O–H···O indicated that the intramolecular hydrogen bond was strengthened in the S1 state. Our calculated results accurately reproduced the experimental absorbance and fluorescence emission spectra, demonstrating that the adopted time-dependent density functional theory (TDDFT) method is reasonable and effective. In addition, qualitative and quantitative intramolecular charge transfer based on the frontier molecular orbitals provided the possibility of the ESIPT reaction. The potential energy curves of the ground and first excited states have been constructed to illustrate the ESIPT mechanism. Based on our calculations, we explain the equilibrium ESIPT processes observed in previous experiments.

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant Nos. 11304135 and 21271095), the Doctor Subject Foundation of the Ministry of Education of China (20132101110001), the Shenyang Natural Science Foundation of China (F15-199-1-04) and the Liaoning Provincial Department of Education Project (Grant No. L2015200).

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Authors and Affiliations

  1. Department of Physics, Liaoning University, Shenyang, People’s Republic of China

    Meixia Zhang, Qiao Zhou & Peng Song

  2. Department of Chemistry, Liaoning University, Shenyang, People’s Republic of China

    Yi Jiang

  3. Normal College, Shenyang University, Shenyang, 110044, People’s Republic of China

    Mengru Zhang & Yumei Dai

  4. Liaoning Key Laboratory of Semiconductor Light Emitting and Photocatalytic Materials, Liaoning University, Shenyang, 110036, People’s Republic of China

    Peng Song

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

    Peng Song

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  1. Meixia Zhang
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  2. Qiao Zhou
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  4. Yumei Dai
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  5. Peng Song
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Correspondence to Peng Song or Yi Jiang.

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Zhang, M., Zhou, Q., Zhang, M. et al. Theoretical Investigation of the ESIPT Mechanism for the 1-Hydroxy-9H-fluoren-9-one and 1-Hydroxy-11H-benzo[b]fluoren-11-one Chromophores. J Clust Sci 28, 1191–1200 (2017). https://doi.org/10.1007/s10876-016-1122-8

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  • DOI: https://doi.org/10.1007/s10876-016-1122-8

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