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Exploring and elaborating the novel excited state dynamical behavior for bisflavonol system

Abstract

In this work, we investigate the dual hydrogen bonded $1$,$4$-bis-($3$-hydroxy-$4$-oxo-$4$H-chromen-$2$-yl)-benzene (bisflavonol) system in detail. Via optimizing stable structures and constructing potential energy curves, we confirm two primary structures (i.e., Anti-bisflavonol and Syn-bisflavonol) can coexist in the S$_0$ state. Calculating the reduced density gradient (RDG) versus sign($\lambda_2$)$\rho$ and gradient isosurfaces, we confirm the formation of double hydrogen bonds for both Anti-bisflavonol and Syn-bisflavonol. Comparing the primary geometrical parameters involved in hydrogen bonds, we verify the double intramolecular hydrogen bonds should be strengthened in the S$_1$ state. In view of the photo-excitation process, we find the charge redistributions around hydrogen bonded moieties of both Anti-bisflavonol and Syn-bisflavonol facilitate the excited state intramolecular proton transfer (ESIPT) reaction. Given reaction paths for ESIPT process, the S$_0$-state and S$_1$-state potential energy surfaces (PESs) are constructed for both Anti-bisflavonol and Syn-bisflavonol along with two hydrogen bonds to reveal the excited state dynamical overall perspective. Searching the transition state (TS) structure and calculating intrinsic reaction coordinate (IRC) energetic profile, we confirm the ESIPT reaction. Combining with Born-Oppenheimer molecular dynamics (BOMD) simulations, we study the ESIPT dynamical behaviors in detail. We present that only the single proton transfer process occurs in the S$_1$ state in aprotic solvents, which makes up for the deficiency of previous experiment. The theoretical electronic spectra further confirm our attribution. This work not only illustrates that the S$_0$-state coexisting Anti-bisflavonol and Syn-bisflavonol can promote respective ESIPT reaction, but also makes a new attribution to previous experiment.

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Publication details

The article was received on 09 Jul 2018, accepted on 07 Aug 2018 and first published on 08 Aug 2018


Article type: Research Article
DOI: 10.1039/C8QO00688A
Citation: Org. Chem. Front., 2018, Accepted Manuscript
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    Exploring and elaborating the novel excited state dynamical behavior for bisflavonol system

    J. Zhao, H. Dong, H. Yang and Y. Zheng, Org. Chem. Front., 2018, Accepted Manuscript , DOI: 10.1039/C8QO00688A

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