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题名: Competitive excited-state single or double proton transfer mechanisms for bis-2,5-(2-benzoxazolyl)-hydroquinone and its derivatives
作者: Zhao, Jinfeng1;  Chen, Junsheng1;  Liu, Jianyong1;  Hoffmann, Mark R.2
刊名: PHYSICAL CHEMISTRY CHEMICAL PHYSICS
发表日期: 2015
DOI: 10.1039/c4cp05651e
卷: 17, 期:18, 页:11990-11999
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Physical ;  Physics, Atomic, Molecular & Chemical
研究领域[WOS]: Chemistry ;  Physics
英文摘要: The excited state intramolecular proton transfer (ESIPT) mechanisms of 2-(2-hydroxyphenyl) benzoxazole (HBO), bis-2,5-(2-benzoxazolyl)-hydroquinone (BBHQ) and 2,5-bis(50-tert-butyl-benzoxazol-20-yl)hydroquinone (DHBO) have been investigated using time-dependent density functional theory (TDDFT). The calculated vertical excitation energies based on the TDDFT method reproduced the experimental absorption and emission spectra well. Three kinds of stable structures were found on the S-1 state potential energy surface (PES). A new ESIPT mechanism that differs from the one proposed previously (Mordzinski et al., Chem. Phys. Lett., 1983, 101, 291. and Lim et al., J. Am. Chem. Soc., 2006, 128, 14542.) is proposed. The new mechanism includes the possibility of simultaneous double proton transfer, or successive single transfers, in addition to the accepted single proton transfer mechanism. Hydrogen bond strengthening in the excited state was based on primary bond lengths, angles, IR vibrational spectra and hydrogen bond energy. Intramolecular charge transfer based on the frontier molecular orbitals (MOs) also supports the proposed mechanism of the ESIPT reaction. To further elucidate the proposed mechanism, reduced dimensionality PESs of the S-0 and S-1 states were constructed by keeping the O-H distance fixed at a series of values. The potential barrier heights among the local minima on the S-1 surface imply competitive single and double proton transfer branches in the mechanism. Based on the new ESIPT mechanism, the observed fluorescence quenching can be satisfactorily explained.
关键词[WOS]: PHOTOINDUCED ELECTRON-TRANSFER ;  SENSING MECHANISM ;  HYDROGEN-BOND ;  TD-DFT ;  RAMAN-SPECTROSCOPY ;  BORATE COMPLEXES ;  2-(2'-HYDROXYPHENYL)BENZOXAZOLE HBO ;  FLUORESCENT CHEMOSENSOR ;  ANISOTROPIC DIELECTRICS ;  POLYMER CONFORMATION
语种: 英语
WOS记录号: WOS:000353767500008
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/146214
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.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Mol React Dynam, Dalian 116023, Liaoning, Peoples R China
2.Univ N Dakota, Dept Chem, Grand Forks, ND 58202 USA

Recommended Citation:
Zhao, Jinfeng,Chen, Junsheng,Liu, Jianyong,et al. Competitive excited-state single or double proton transfer mechanisms for bis-2,5-(2-benzoxazolyl)-hydroquinone and its derivatives[J]. PHYSICAL CHEMISTRY CHEMICAL PHYSICS,2015,17(18):11990-11999.
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