DICP OpenIR
The effects of the heteroatom and position on excited-state intramolecular proton transfer of new hydroxyphenyl benzoxazole derivatives: a time-dependent density functional theory study
Li, Changming1,2; Guo, Wei1; Zhou, Panwang3; Tang, Zhe3
Corresponding AuthorGuo, Wei(vella99@163.com)
Source PublicationORGANIC CHEMISTRY FRONTIERS
2019-06-07
ISSN2052-4129
DOI10.1039/c9qo00295b
Volume6Issue:11Pages:1807-1815
Funding ProjectNational Natural Science Foundation of China[11704178] ; Natural Science Foundation of Hunan[2018JJ2312]
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan
WOS SubjectChemistry, Organic
WOS Research AreaChemistry
WOS KeywordGAUSSIAN-BASIS SETS ; TRANSFER MECHANISM ; FEMTOSECOND DYNAMICS ; ASYMMETRIC STRUCTURE ; REACTIVE DYES ; BASE-PAIRS ; ATOMS LI ; FLUORESCENCE ; ESIPT ; PROBES
AbstractThe effects of the heteroatom and position on excited-state intramolecular proton transfer (ESIPT) of 2-[4 '-(N-4,6-dichloro-1,3,5-triazi-n-2-yl)2 ' hydroxyphenyl]benzoxazole (4THBO) have been investigated via time-dependent density functional theory studies. The heteroatoms refer to O and S atoms, and the position effect refers to the N-4,6-trichloro-1,3,5-triazin-2-yl (TCT) substituents in the para and meta positions. The configuration of the four compounds (4THBO, 4THBT, 5THBO and 5THBT) was optimized and the bond lengths, bond angles and infrared spectra of the atoms participating in the proton transfer in the S0 and S1 states were studied. The occurrence of ultrafast ESIPT in the four compounds was demonstrated. Moreover, the potential energy curves of the S0 and S1 states were constructed, and the effects of the heteroatom substitution and substituent position changes on the ESIPT mechanism of the four 4THBO derivatives were analyzed. The results show that the ESIPT barrier of the S atom substitution in the excited state is lower than that of the O atom-substituted molecule, and the energy barrier of the substituent (TCT) in the meta-position is significantly smaller than that in the para-position. These results indicate that the substitution of the S heteroatom promotes the ESIPT of the 4THBO compound and that the substituent (TCT) in the para position is more prone to proton transfer than that in the meta position. Our work could provide a theoretical basis for further experiments.
Language英语
Funding OrganizationNational Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan ; National Natural Science Foundation of China ; National Natural Science Foundation of China ; Natural Science Foundation of Hunan ; Natural Science Foundation of Hunan
WOS IDWOS:000469257000009
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/172156
Collection中国科学院大连化学物理研究所
Corresponding AuthorGuo, Wei
Affiliation1.Univ South China, Sch Elect Engn, Hengyang 421001, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
3.Shandong Univ, Inst Mol Sci & Engn, Qingdao 266235, Shandong, Peoples R China
Recommended Citation
GB/T 7714
Li, Changming,Guo, Wei,Zhou, Panwang,et al. The effects of the heteroatom and position on excited-state intramolecular proton transfer of new hydroxyphenyl benzoxazole derivatives: a time-dependent density functional theory study[J]. ORGANIC CHEMISTRY FRONTIERS,2019,6(11):1807-1815.
APA Li, Changming,Guo, Wei,Zhou, Panwang,&Tang, Zhe.(2019).The effects of the heteroatom and position on excited-state intramolecular proton transfer of new hydroxyphenyl benzoxazole derivatives: a time-dependent density functional theory study.ORGANIC CHEMISTRY FRONTIERS,6(11),1807-1815.
MLA Li, Changming,et al."The effects of the heteroatom and position on excited-state intramolecular proton transfer of new hydroxyphenyl benzoxazole derivatives: a time-dependent density functional theory study".ORGANIC CHEMISTRY FRONTIERS 6.11(2019):1807-1815.
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