The substituent effect on the excited state intramolecular proton transfer of 3-hydroxychromone

doi:10.1088/1674-1056/ab3434

Abstract

The excited state intramolecular proton transfer of four derivatives (FM, BFM, BFBC, CCM) of 3-hydroxychromone is investigated. The geometries of different substituents are optimized to study the substituent effects on proton transfer. The mechanism of hydrogen bond enhancement is qualitatively elucidated by comparing the infrared spectra, the reduced density gradient, and the frontier molecular orbitals. The calculated electronic spectra are consistent with the experimental results. To quantify the proton transfer, the potential energy curves (PECs) of the four derivatives in S₀ and S₁ states are scanned. It is concluded that the ability of proton transfer follows the order:FM > BFM > BFBC > CCM.

Keywords: excited state intramolecular proton transfer (ESIPT) hydrogen bond reduced density gradient (RDG) substituents

Received: 13 June 2019
Revised: 05 July 2019
Accepted manuscript online:

PACS:	31.15.ae	(Electronic structure and bonding characteristics)
	31.15.A-	(Ab initio calculations)
	31.15.es	(Applications of density-functional theory (e.g., to electronic structure and stability; defect formation; dielectric properties, susceptibilities; viscoelastic coefficients; Rydberg transition frequencies))

Fund:

Project supported by the National Natural Science Foundation of China (Grant Nos. 11874241, 11847224, and 11804195), the Shandong Province Higher Educational Science and Technology Program, China (Grant No. J15LJ03), the Taishan Scholar Project of Shandong Province, China, China Post-Doctoral Foundation (Grant No. 2018M630796), and the Natural Science Foundation of Shandong Province, China (Grant No. ZR2018BA034).

Corresponding Authors: Yuzhi Song, Yuzhi Song
E-mail: yzsong@sdnu.edu.cn;dujun@sdnu.edu.cn

Cite this article:

Yuzhi Song(宋玉志), Songsong Liu(刘松松), Jiajun Lu(陆佳骏), Hui Zhang(张慧), Changzhe Zhang(张常哲), Jun Du(杜军) The substituent effect on the excited state intramolecular proton transfer of 3-hydroxychromone 2019 Chin. Phys. B 28 093102

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The substituent effect on the excited state intramolecular proton transfer of 3-hydroxychromone

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