Excited-state Intramolecular Proton Transfer Mechanisms of Thiazole-basedChemosensor: a TD-DFT Study

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摘要

The excited-state intramolecular proton transfer (ESIPT) mechanisms of 2-(2-hydroxyphenyl)-4- phenylthiazole (HPT) and 2-(5-bromo-2-hydroxyphenyl)-4-phenylthiazole (BrHPT) have been systematically investigated by density functional theory (DFT) and time-dependent density functional theory (TDDFT) methods, approaching along with the polarizable continuum model (PCM). The calculated primary bond lengths and bond angles demonstrate that HPT and BrHPT can form intramolecular hydrogen bonds in the ground state (S0), which can be significantly strengthened in the first excited state (S1). Our calculated results well reproduce the experimental absorption and emission spectra. Upon addition of F-, the proton can move close to F- and the hydroxy moieties are deprotonated, which cause a red-shift in absorption and a new emission peak in ﬂuorescence emission with the disappearance of the dual fluorescence emission. The calculated Mulliken’s charge distribution and frontier molecular orbitals further demonstrate that the ESIPT processes are more likely to occur in the S1 state. The constructed potential energy curves of the S0 and S1 states confirm that the proton transfer processes are hard to occur in the S0 state due to the high energy barriers. Moreover, much lower energy barriers are found in the S1 state, which proves that the ESIPT processes are more likely to take place in the S1 state. In addition, compound with electron withdrawing (–Br) group might result in much stronger intramolecular hydrogen bond and owns lower energy barrier, which can facilitate the ESIPT processes.

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	曹虎
	刘改梅
	蔡佳
	王艳

关键词 ： density functional theory, ESIPT, 2-(2-hydroxy-phenyl)-4-phenylthiazole, potential energy curves

Abstract：

Key words： density functional theory ESIPT 2-(2-hydroxy-phenyl)-4-phenylthiazole potential energy curves

收稿日期: 2020-04-07 出版日期: 2020-11-09

基金资助:This work was supported by the National Natural Science Foundation of China (No. 21963008), the Natural Science Foundation of Hubei Province(No. 2016CFB400) and the College Students’ Innovative Entrepreneurial Training Plan Program of Hubei Minzu University ( Nos. 2016CX066 and X201910517140)

通讯作者: hbwangy@sohu.com E-mail: hbmdwangy@aliyun.com

引用本文:

曹虎;刘改梅;蔡佳;王艳. Excited-state Intramolecular Proton Transfer Mechanisms of Thiazole-basedChemosensor: a TD-DFT Study[J]. 结构化学, 2020, 39(11): 1933-1940.
CAO Hu;LIU Gai-Mei;CAI Jia;WANG Yan. Excited-state Intramolecular Proton Transfer Mechanisms of Thiazole-basedChemosensor: a TD-DFT Study. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2020, 39(11): 1933-1940.

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http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2020/V39/I11/1933

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