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Effects of different environments on excited-state intramolecular proton transfer of 4′-methoxy-3-hydroxyflavone

Abstract

Recently, the fluorescence properties in different solvents of the 4'-methoxy-3-hydroxyflavone dye had been observed in experiment (Phys. Chem. Chem. Phys., 2018, 20, 7885-7895). However, the corresponding reaction mechanisms are lacking. In this research, we investigated effects of different solvent environments on excited-state intramolecular proton transfer for the first time for 4'-methoxy-3-hydroxyflavone. The calculated absorption and emission spectral values are matched to the experimental data. Calculated the hydrogen bond lengths and angles confirm the excited state hydrogen bond strengthening mechanism. The frontier molecular orbitals display the redistribution of electron density in different solvents, affecting photophysical properties of this dye. The infrared vibrational spectra and the RDG isosurfaces are analyzed, which illustrate in excited state the intensity of the hydrogen bond decreases gradually as solvent polarity increasing. And the potential energy curves indicate that the excited state intramolecular proton transfer reaction is increasingly difficult to occur in these solvents: Toluene →ACN →DMF.

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Publication details

The article was received on 16 Oct 2018, accepted on 03 Dec 2018 and first published on 04 Dec 2018


Article type: Research Article
DOI: 10.1039/C8QO01111G
Citation: Org. Chem. Front., 2018, Accepted Manuscript
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    Effects of different environments on excited-state intramolecular proton transfer of 4′-methoxy-3-hydroxyflavone

    Y. Chen, Y. Yang, Y. Zhao, S. Liu and Y. Li, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO01111G

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