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题名: A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin
作者: Yang, Dapeng1, 3;  Yang, Guang2;  Zhao, Jinfeng3;  Zheng, Rui1;  Wang, Yusheng1;  Lv, Jian1
关键词: AIM ;  ESIPT ;  IR vibrational spectra ;  MOs ;  potential energy curves
刊名: JOURNAL OF PHYSICAL ORGANIC CHEMISTRY
发表日期: 2017-11-01
DOI: 10.1002/poc.3684
卷: 30, 期:11
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic ;  Chemistry, Physical
研究领域[WOS]: Chemistry
英文摘要: In the present work, we investigate a new chromophore (ie, quercetin) (Simkovitch et al J Phys Chem B 119 [2015] 10244) about its complex excited-state intramolecular proton transfer (ESIPT) process based on density functional theory and time-dependent density functional theory methods. On the basis of the calculation of electron density rho(r) and Laplacian del(2)rho(r) at the bond critical point using atoms-in-molecule theory, the intramolecular hydrogen bonds (O-1-H2 center dot center dot center dot O5 and O-3-H4 center dot center dot center dot O5) have been supported to be formed in the S-0 state. Comparing the prime structural variations of quercetin involved in its 2 intramolecular hydrogen bonds, we find that these 2 hydrogen bonds should be strengthened in the S-1 state, which is a fundamental precondition for facilitating the ESIPT process. Concomitantly, infrared vibrational spectra analysis further verifies this viewpoint. In good agreement with previous experimental spectra results, we find that quercetin reveals 2 kinds of excited-state structures (quercetin* and quercetin-PT1*) in the S-1 state. Frontier molecular orbitals depict the nature of electronically excited state and support the ESIPT reaction. Our scanned potential energy curves according to variational O-1-H-2 and O-3-H-4 coordinates demonstrate that the proton transfer process should be more likely to occur in the S-1 state via hydrogen bond wire O-1-H2 center dot center dot center dot O5 rather than O-3-H4 center dot center dot center dot O5 because of the lower potential energy barrier 2.3kcal/mol. Our present work explains previous experimental result and makes up the deficiency of mechanism in previous experiment. In the end, we make a reasonable assignment for ESIPT process of quercetin.
关键词[WOS]: DENSITY-FUNCTIONAL THEORY ;  HYDROGEN-BONDING DYNAMICS ;  PIGMENT YELLOW 101 ;  ANISOTROPIC DIELECTRICS ;  FLUORESCENCE PROBE ;  SENSING MECHANISM ;  ELECTRON-DENSITY ;  CHARGE-TRANSFER ;  ACID SYSTEM ;  TD-DFT
语种: 英语
WOS记录号: WOS:000412844400004
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/150229
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.North China Univ Water Resources & Elect Power, Coll Math & Informat Sci, Zhengzhou 450045, Henan, Peoples R China
2.Jiaozuo Univ, Dept Basic Sci, Jiaozuo 454000, Peoples R China
3.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam Theoret & Computat, Dalian 116023, Peoples R China

Recommended Citation:
Yang, Dapeng,Yang, Guang,Zhao, Jinfeng,et al. A theoretical assignment on excited-state intramolecular proton transfer mechanism for quercetin[J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY,2017,30(11).
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