Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine

doi:10.1016/j.jphotochem.2018.08.028

	Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine
	Wang, Yi 1; Tang, Zhe 1,2; Lu, Meiheng 2; Liu, Kangjing 4; Zhao, Yanliang 2; Qi, Yutai 1; Zhang, Peng 3; Zhou, Panwang2
刊名	JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
	2018-12-01
卷号	367 页码:261-269
关键词	ESIPT Molecular electrostatic potential surface Frontier molecular orbitals Potential-energy curves
ISSN号	1010-6030
DOI	10.1016/j.jphotochem.2018.08.028
通讯作者	Wang, Yi(wangyi_dlpu@163.com) ; Zhang, Peng(jutzp@sina.com) ; Zhou, Panwang(pwzhou@dicp.ac.cn)
英文摘要	The excited-state intramolecular proton transfer (ESIPT) dynamics of 2-(4'-Amino-2'-hydroxyphenyI)-1H-imidazo-[4,5-c]pyridine (AHPIP-c) has been studied by using density-functional theory and time-dependent density-functional theory method. Three kinds of different polar aprotic solvents, including acetonitrile (strong polar), tetrahydrofuran (weak polar) and methylcyclohexane (non-polar) have been chosen to explore solvent effects on these molecules. The calculated absorption and fluorescence spectra agree well with the experimental results for the three solvents and the dual fluorescence emission mechanism is well explained. The electron density p(r) and Laplacian del(2)rho(r) at the bond critical point (BCP) have been calculated using the Atoms-In-Molecule (AIM) theory, which prove that the intramolecular hydrogen bond (O-1-H-2 center dot center dot center dot N-3) exists in the S-0 state. The geometric parameters and the infrared vibrational spectra in the O-H stretching vibrational region have been calculated, which manifests the hydrogen-bond is strengthened in the S-1 state. The molecular electrostatic potential surface and frontier molecular orbitals analysis demonstrate that the proton transfer prefer occurring on excited state because of the charge redistribution upon photo-excitation. The results of potential energy curves, further confirm that the proton transfer process is more likely to conduct in the S-1 state due to the lower potential energy barrier than that in the S-0 state. In addition, we also find that ESIPT reaction is more easily to occur as the solvent polarity decreases. Therefore, we believe that solvent effect could play an important role in controlling excited state behaviors of AHPIP-c molecules.
资助项目	Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China[21773238]
WOS关键词	INTRAMOLECULAR PROTON-TRANSFER ; EXCITED-STATE ; CHARGE-TRANSFER ; FLUORESCENT CHEMOSENSOR ; SENSING MECHANISM ; TD-DFT ; SOLVENT ; FLUORIDE ; 2-(2-HYDROXYPHENYL)BENZIMIDAZOLE ; SPECTROSCOPY
WOS研究方向	Chemistry
语种	英语
出版者	ELSEVIER SCIENCE SA
WOS记录号	WOS:000450377500031
资助机构	Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; Open Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; 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/321008/166470]
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; Zhang, Peng; Zhou, Panwang
作者单位	1.Dalian Polytech Univ, Sch Biol Engn, Dalian 116034, Peoples R China 2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China 3.Dalian Polytech Univ, Sch Mech Engn & Automat, Dalian 116034, Peoples R China 4.Dalian Polytech Univ, Sch Food Sci & Technol, Dalian 116034, Peoples R China
推荐引用方式 GB/T 7714	Wang, Yi,Tang, Zhe,Lu, Meiheng,et al. Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine[J]. JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY,2018,367:261-269.
APA	Wang, Yi.,Tang, Zhe.,Lu, Meiheng.,Liu, Kangjing.,Zhao, Yanliang.,...&Zhou, Panwang.(2018).Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine.JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY,367,261-269.
MLA	Wang, Yi,et al."Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine".JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY 367(2018):261-269.