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Excited state intramolecular proton transfer and substituent effect of 10-hydroxybenzo[h]quinoline: A time-dependent density functional theory study
Chai, Shuo1,2; Cong, Shu-Lin1
KeywordExcited State Intramolecular Proton Transfer Hydrogen Bond Substituent Effect Time-dependent Density Functional Theory
Source PublicationCOMPUTATIONAL AND THEORETICAL CHEMISTRY
2014-04-15
DOI10.1016/j.comptc.2014.02.019
Volume1034Pages:80-84
Indexed BySCI
SubtypeArticle
WOS HeadingsScience & Technology ; Physical Sciences
WOS SubjectChemistry, Physical
WOS Research AreaChemistry
WOS KeywordTRANSFER ESIPT ; CHARGE-TRANSFER ; FLUORESCENCE ; DERIVATIVES ; DYNAMICS ; ELECTRON ; COMPLEXES ; SOLVENTS ; ANALOGS ; SYSTEMS
AbstractThe excited state intramolecular proton transfer (ESIPT) and the substituent effect of 10-hydroxybenzo[h]quinoline (HBQ) compounds are investigated using the time-dependent density functional theory (TDDFT) method. With the spectra and potential energy curve calculations we have demonstrated the occurrence of an ultrafast excited state intramolecular proton transfer reaction in HBQ compounds. The HBQ-a and HBQ-b in the enol conformations can convert into the keto tautomers in the excited state S-1. The significant Stokes shift of HBQ-a is observed, as large as 300 nm, which is much larger than that of HBQ-b. The calculated molecular orbital gap between the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) for HBQ-a is 3.33 eV, smaller than the 3.79 eV for HBQ-b. The calculations demonstrate that it is much easier to take place the ESIPT reaction for HBQ-a than HBQ-b. The reaction mechanism of ESIPT is analyzed with theoretical potential energy curves and the ESIPT reaction energy barriers of 3.73 kcal/mol for HBQ-a and 17.75 kcal/mol for HBQ-b are obtained. These results clearly indicate that the substituent with electron-withdrawing groups in the hydrogen-accepting moiety in HBQ-a facilitate the proton transfer in the excited state. (C) 2014 Elsevier B.V. All rights reserved.
Language英语
WOS IDWOS:000334989600010
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://cas-ir.dicp.ac.cn/handle/321008/145716
Collection中国科学院大连化学物理研究所
Affiliation1.Dalian Univ Technol, Sch Phys & Optoelect Technol, Dalian 116024, Peoples R China
2.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Peoples R China
Recommended Citation
GB/T 7714
Chai, Shuo,Cong, Shu-Lin. Excited state intramolecular proton transfer and substituent effect of 10-hydroxybenzo[h]quinoline: A time-dependent density functional theory study[J]. COMPUTATIONAL AND THEORETICAL CHEMISTRY,2014,1034:80-84.
APA Chai, Shuo,&Cong, Shu-Lin.(2014).Excited state intramolecular proton transfer and substituent effect of 10-hydroxybenzo[h]quinoline: A time-dependent density functional theory study.COMPUTATIONAL AND THEORETICAL CHEMISTRY,1034,80-84.
MLA Chai, Shuo,et al."Excited state intramolecular proton transfer and substituent effect of 10-hydroxybenzo[h]quinoline: A time-dependent density functional theory study".COMPUTATIONAL AND THEORETICAL CHEMISTRY 1034(2014):80-84.
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