A DFT/TD-DFT study of effect of different substituent on ESIPT fluorescence features of 2-(2'-hydroxyphenyl)-4-chloro- methylthiazole derivatives

doi:10.1088/1674-1056/ac21c6

Abstract Based on density functional theory (DFT) and time-dependent density functional theory (TD-DFT), the effects of substituent on the excited-state intramolecular proton transfer (ESIPT) process and photophysical properties of 2-(2'-hydroxyphenyl)-4-chloromethylthiazole (HCT) are studied. The electron-donating group (CH₃, OH) and electron-withdrawing group (CF₃, CHO) are introduced to analyze the changes of intramolecular H-bond, the frontier molecular orbitals, the absorption/fluorescence spectra, and the energy barrier of ESIPT process. The calculation results indicate that electron-donating group strengthens the intramolecular H-bond in the S₁ state, and leads to an easier ESIPT process. The electron-withdrawing group weakens the corresponding H-bond and makes ESIPT process a little harder. Different substituents also affect the photophysical properties of HCT. The electron-withdrawing group (CF₃, CHO) has a little effect on electronic spectra. The electron-donating group (CH₃, OH) red-shifts both the absorption and fluorescence emission peaks of HCT, respectively, which causes the Stokes shift to increase.

Keywords: excited-state intramolecular proton transfer (ESIPT) TD-DFT substitution

Received: 15 May 2021
Revised: 15 May 2021
Accepted manuscript online: 27 August 2021

PACS:	82.39.Jn	(Charge (electron, proton) transfer in biological systems)
	31.15.ee	(Time-dependent density functional theory)
	87.15.ht	(Ultrafast dynamics; charge transfer)

Corresponding Authors: Shen-Yang Su
E-mail: susanfang20@gmail.com

Cite this article:

Shen-Yang Su(苏申阳), Xiu-Ning Liang(梁秀宁), and Hua Fang(方华) A DFT/TD-DFT study of effect of different substituent on ESIPT fluorescence features of 2-(2'-hydroxyphenyl)-4-chloro- methylthiazole derivatives 2022 Chin. Phys. B 31 038202

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A DFT/TD-DFT study of effect of different substituent on ESIPT fluorescence features of 2-(2'-hydroxyphenyl)-4-chloro- methylthiazole derivatives

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