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A theoretical study of the ESIPT mechanism of 3-hydroxyflavone derivatives: solvation effect and the importance of TICT for its dual fluorescence properties

文献类型：期刊论文

作者Qi, Yutai2; Lu, Meiheng3,4; Wang, Yi2; Tang, Zhe5; Gao, Ziqing2; Tian, Jing2; Fei, Xu1; Li, Yao6; Liu, Jianyong3
刊名ORGANIC CHEMISTRY FRONTIERS
出版日期2019-09-07
卷号6期号:17页码:3136-3143
ISSN号2052-4129
DOI10.1039/c9qo00634f
通讯作者Wang, Yi(wangyi@dlpu.edu.cn) ; Liu, Jianyong(beam@dicp.ac.cn)
英文摘要In this paper, the excited-state intramolecular proton transfer (ESIPT) process and the solvatochromic effect of 2-(4-(diethylamino)phenyl)-3-hydroxy-4H-chromen-4-one (DHC) molecules were reported by the density functional theory and time-dependent density functional theory method. We optimized the structures in four kinds of solvents, and the recorded absorption and fluorescence spectra were in agreement with the experiments. By establishing the potential energy curve, we proved that this fluorescent probe was designed based on the ESIPT process of the parent molecule DHC. A deeper study of the ESIPT process revealed that the energy consumed by the molecules along the C5-C18 bond twist was an important part of the dual fluorescence characteristics of the DHC, and the geometric structure tended to be planar with the decrease of the dielectric constant of the solvent. The effect of solvent media on electronic transition energies and absorption as well as florescence spectra were presented. As we know, a driving force of the proton transfer reaction was provided by hydrogen bonding. By comparing the infrared vibration spectrum, bond length and bond angle, we found that the hydrogen bond was enhanced after photoexcitation and was gradually increased as the solvent dielectric constant decreased (dimethylsulfoxide (DMSO) < acetonitrile (ACN) < dichloromethane (DCM) < 1,4-dioxane (DIO)), which was also evidenced by the reduced density gradient function (RDG) isosurface and scatter plots. Therefore, the process of ESIPT reaction was controlled by the solvent. Furthermore, the effect of the solvent on ESIPT was explained by comparing the reaction energy barrier in four kinds of solvents. The results showed that ESIPT was more likely to occur as the solvent dielectric constant decreased.
WOS关键词INTRAMOLECULAR PROTON-TRANSFER ; GAUSSIAN-BASIS SETS ; EXCITED-STATE ; CHARGE-TRANSFER ; TRANSITION-STATES ; ELECTRON-TRANSFER ; ATOMS LI ; SOLVENTS ; FLUORIDE ; PROBES
资助项目Liaoning Province Natural Science Foundation[20180550765] ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China[31771914]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000483840200011
出版者ROYAL SOC CHEMISTRY
资助机构Liaoning Province Natural Science Foundation ; Liaoning Province Natural Science Foundation ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Liaoning Province Natural Science Foundation ; Liaoning Province Natural Science Foundation ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Liaoning Province Natural Science Foundation ; Liaoning Province Natural Science Foundation ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Liaoning Province Natural Science Foundation ; Liaoning Province Natural Science Foundation ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2019 (Open Project of the State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China
源URL[http://cas-ir.dicp.ac.cn/handle/321008/172963]  
专题大连化学物理研究所_中国科学院大连化学物理研究所
通讯作者Wang, Yi; Liu, Jianyong
作者单位1.Dalian Polytech Univ, Network Informat Ctr, Dalian, Peoples R China
2.Dalian Polytech Univ, Sch Biol Engn, Dalian 116034, Peoples R China
3.Chinese Acad Sci, State Key Lab Mol React Dynam, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
4.Shenyang Univ Chem Technol, Coll Appl Chem, Shenyang 110142, Liaoning, Peoples R China
5.Shandong Univ, Inst Mol Sci & Engn, Qingdao 266237, Shandong, Peoples R China
6.Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian, Peoples R China
推荐引用方式
GB/T 7714		 Qi, Yutai,Lu, Meiheng,Wang, Yi,et al. A theoretical study of the ESIPT mechanism of 3-hydroxyflavone derivatives: solvation effect and the importance of TICT for its dual fluorescence properties[J]. ORGANIC CHEMISTRY FRONTIERS,2019,6(17):3136-3143.
APA Qi, Yutai.,Lu, Meiheng.,Wang, Yi.,Tang, Zhe.,Gao, Ziqing.,...&Liu, Jianyong.(2019).A theoretical study of the ESIPT mechanism of 3-hydroxyflavone derivatives: solvation effect and the importance of TICT for its dual fluorescence properties.ORGANIC CHEMISTRY FRONTIERS,6(17),3136-3143.
MLA Qi, Yutai,et al."A theoretical study of the ESIPT mechanism of 3-hydroxyflavone derivatives: solvation effect and the importance of TICT for its dual fluorescence properties".ORGANIC CHEMISTRY FRONTIERS 6.17(2019):3136-3143.

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来源：大连化学物理研究所

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