DICP OpenIR
Solvation effect on the ESIPT mechanism of 2-(4 '-amino-2 '-hydroxyphenyl)-1H-imidazo- [4,5-c]pyridine
Tang, Zhe1,2; Lu, Meiheng2; Liu, Kangjing4; Zhao, Yanliang2; Qi, Yutai1; Wang, Yi1; Zhang, Peng3; Zhou, Panwang2
Corresponding AuthorWang, Yi(wangyi_dlpu@163.com) ; Zhang, Peng(jutzp@sina.com) ; Zhou, Panwang(pwzhou@dicp.ac.cn)
KeywordESIPT Molecular electrostatic potential surface Frontier molecular orbitals Potential-energy curves
Source PublicationJOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
2018-12-01
ISSN1010-6030
DOI10.1016/j.jphotochem.2018.08.028
Volume367Pages:261-269
Funding ProjectOpen Project of SKLMRD-K2018 (Open Project of State Key Laboratory of Molecular Reaction Dynamics) ; National Natural Science Foundation of China[21773238]
Funding OrganizationOpen 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
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordINTRAMOLECULAR PROTON-TRANSFER ; EXCITED-STATE ; CHARGE-TRANSFER ; FLUORESCENT CHEMOSENSOR ; SENSING MECHANISM ; TD-DFT ; SOLVENT ; FLUORIDE ; 2-(2-HYDROXYPHENYL)BENZIMIDAZOLE ; SPECTROSCOPY
AbstractThe 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.
Language英语
Funding OrganizationOpen 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
WOS IDWOS:000450377500031
PublisherELSEVIER SCIENCE SA
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Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/166471
Collection中国科学院大连化学物理研究所
Corresponding AuthorWang, Yi; Zhang, Peng; Zhou, Panwang
Affiliation1.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
Recommended Citation
GB/T 7714
Tang, Zhe,Lu, Meiheng,Liu, Kangjing,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 Tang, Zhe.,Lu, Meiheng.,Liu, Kangjing.,Zhao, Yanliang.,Qi, Yutai.,...&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 Tang, Zhe,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.
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