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Tunable ESIPT reaction and antioxidant activities of 3-hydroxyflavone and its derivatives by altering atomic electronegativity

Abstract

The influences of atomic electronegativity (O, S and Se atoms) on the excited state intramolecular proton transfer (ESIPT) properties of three compounds (3-HF, 3-HTF and 3-HSeF) were systematically studied by using the density functional theory (DFT) and time-dependent DFT (TD-DFT) methods. Furthermore, the antioxidant activities of the three compounds were evaluated by using different parameters from the perspective of biological activity. Calculated results indicate that the generation of ESIPT originates from the excited state intramolecular charge transfer owing to the change of electron density distribution on the frontier molecular orbitals and natural bond orbital (NBO) charge distribution of the O1 and O2 atoms at S0 and S1 states. Moreover, 3-HTF shows the greatest red shift of the O1-H1 stretching peak and the lowest energy barrier at the S1 state among the three compounds, implying that 3-HTF would have the strongest intramolecular hydrogen bond at S1 state, which is most beneficial to the occurrence of ESIPT. In addition, the decreased ionization potentials and energy gaps from 3-HF to 3-HTF and 3-HSeF means that the antioxidant activity of the compound would be enhanced along with the lowered atomic electronegativity. Interestingly, the lower ionization potentials and energy gaps of the compounds in keto forms suggest that the compound easy to carry out ESIPT reaction would exhibit the efficient antioxidant activity, which would establish the relationship between ESIPT reaction and antioxidant activity of the compound and provide a new notion for synthesizing more efficient antioxidants in experiment.

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Publication details

The article was received on 13 Sep 2018, accepted on 09 Oct 2018 and first published on 10 Oct 2018


Article type: Research Article
DOI: 10.1039/C8QO00998H
Citation: Org. Chem. Front., 2018, Accepted Manuscript
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    Tunable ESIPT reaction and antioxidant activities of 3-hydroxyflavone and its derivatives by altering atomic electronegativity

    C. Sun, H. Zhao, X. Liu, H. Yin and Y. Shi, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO00998H

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