The theoretical study about the ESIPT mechanism for 2,4-bis(benzooxazol-2 '-yl)hydroquinone: Single or double?

doi:10.1002/poc.3903

	The theoretical study about the ESIPT mechanism for 2,4-bis(benzooxazol-2 '-yl)hydroquinone: Single or double?
	Hao, Jiaojiao; Yang, Yang
刊名	JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
	2019-03-01
卷号	32 期号:3 页码:8
关键词	double ESIPT mechanism intramolecular hydrogen bond single TDDFT
ISSN号	0894-3230
DOI	10.1002/poc.3903
通讯作者	Yang, Yang(light_yang@dicp.ac.cn)
英文摘要	On the basis of the density functional theory (DFT) and time-dependent DFT (TDDFT) methods, we theoretically study the excited-state intramolecular proton transfer (ESIPT) mechanism of 2,4-bis(benzooxazol-2 '-yl)hydroquinone (2,4-DHBO), which is reported in the previous literature (Ulrich et al. New J. Chem. 2016, 40, 5877). The calculated absorption and fluorescence spectra of 2,4-DHBO are accordant with previous experiment, which indicates that the selective theoretical method is credible. The comparisons of the calculated bond lengths, angles, infrared, and Raman vibrational spectra of 2,4-DHBO manifest that two intramolecular hydrogen bonds (HBs) strengthen in the excited state (S-1), which should be triggered the ESIPT reaction. In addition, the calculated frontier molecular orbitals (MOs) and the map of the electron density difference between the ground (S-0) and S-1 states provide that the ESIPT reactions are facilitated by charge transfer after photoexcitation. Moreover, to explore the detailed ESIPT mechanism of 2,4-DHBO, the potential energy surfaces (PESs) in the S-0 and S-1 states are constructed. Because of the low excited-state potential barriers on the PESs of 2,4-DHBO, the single and stepwise double ESIPT mechanisms are revealed in the S-1 state, which is different from single ESIPT mechanism proposed by experiment. We hope the detailed ESIPT mechanism of this fluorophore based on my theoretical research will help researchers to design such kinds of fluorophores in the future.
资助项目	National Natural Science Foundation of China[21403226] ; National Natural Science Foundation of China[21503226]
WOS关键词	INTRAMOLECULAR PROTON-TRANSFER ; EXCITED-STATE SINGLE ; HYDROGEN-BOND ; TD-DFT ; SENSING MECHANISM ; FLUORESCENCE ; LUMINESCENCE ; BEHAVIORS ; CHEMISTRY ; EMISSION
WOS研究方向	Chemistry
语种	英语
出版者	WILEY
WOS记录号	WOS:000458951200008
资助机构	National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; National Natural Science Foundation of China
内容类型	期刊论文
源URL	[http://cas-ir.dicp.ac.cn/handle/321008/166030]
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	Yang, Yang
作者单位	Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
推荐引用方式 GB/T 7714	Hao, Jiaojiao,Yang, Yang. The theoretical study about the ESIPT mechanism for 2,4-bis(benzooxazol-2 '-yl)hydroquinone: Single or double?[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,2019,32(3):8.
APA	Hao, Jiaojiao,&Yang, Yang.(2019).The theoretical study about the ESIPT mechanism for 2,4-bis(benzooxazol-2 '-yl)hydroquinone: Single or double?.JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,32(3),8.
MLA	Hao, Jiaojiao,et al."The theoretical study about the ESIPT mechanism for 2,4-bis(benzooxazol-2 '-yl)hydroquinone: Single or double?".JOURNAL OF PHYSICAL ORGANIC CHEMISTRY 32.3(2019):8.