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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
关键词Excited State Intramolecular Proton Transfer Hydrogen Bond Substituent Effect Time-dependent Density Functional Theory
刊名COMPUTATIONAL AND THEORETICAL CHEMISTRY
2014-04-15
DOI10.1016/j.comptc.2014.02.019
1034页:80-84
收录类别SCI
文章类型Article
WOS标题词Science & Technology ; Physical Sciences
类目[WOS]Chemistry, Physical
研究领域[WOS]Chemistry
关键词[WOS]TRANSFER ESIPT ; CHARGE-TRANSFER ; FLUORESCENCE ; DERIVATIVES ; DYNAMICS ; ELECTRON ; COMPLEXES ; SOLVENTS ; ANALOGS ; SYSTEMS
英文摘要The 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.
语种英语
WOS记录号WOS:000334989600010
引用统计
被引频次:10[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://cas-ir.dicp.ac.cn/handle/321008/145716
专题中国科学院大连化学物理研究所
作者单位1.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
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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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