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Time-Resolved and Mechanistic Study of the Photochemical Uncaging Reaction of the o-Hydroxycinnamic Caged Compound
Yu, Youqing; Wu, Lidan; Zou, Xiaoran; Dai, Xiaojuan; Liu, Kunhui; Su, Hongmei
刊名JOURNAL OF PHYSICAL CHEMISTRY A
2013-08-22
DOI10.1021/jp403323h
117期:33页:7767-7775
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
关键词[WOS]PHOTOREMOVABLE PROTECTING GROUP ; COUMARINIC ACIDS ; SPECTROSCOPY ; PHOTOTRIGGERS ; LACTONIZATION ; PHOTORELEASE ; PHOSPHATES ; ABSORPTION ; MOLECULES ; DYNAMICS
英文摘要The o-hydroxycinnamic derivatives represent efficient caged compounds that can realize quantification of delivery upon uncaging, but there has been lack of time-resolved and mechanistic studies. We used time-resolved infrared (TRIR) spectroscopy to investigate the photochemical uncaging dynamics of the prototype o-hydroxycinnamic compound, (E)-3-(2-hydroxyphenyl)-acrylic acid ethyl ester (HAAEE), leading to coumarin and ethanol upon uncaging. Taking advantage of the specific vibrational marker bands and the IR discerning capability, we have identified and distinguished two key intermediate species, the cis-isomers of HAAEE and the tetrahedral intermediate, in the transient infrared spectra, thus providing clear spectral evidence to support the intramolecular nucleophilic addition mechanism following the trans-cis photoisomerization. Moreover, the product yields of coumarin upon uncaging were observed to be greatly affected by the solvent polarity, suppressed in CH2Cl2 but enhanced in D2O/CH3CN with the increasing volume ratio of D2O. The highly solvent-dependent behavior indicates E1 elimination of the tetrahedral intermediate to give rise to the final uncaging product coumarin. The photorelease rate of coumarin was directly characterized from TRIR (3.6 x 10(6) s(-1)), revealing the promising application of such o-hydroxycinnamic compound in producing fast alcohol jumps. The TRIR results provide the first time-resolved detection and thus offer direct dynamical information about this photochemical uncaging reaction.
语种英语
WOS记录号WOS:000323593700013
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被引频次:2[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/321008/137957
专题中国科学院大连化学物理研究所
作者单位Chinese Acad Sci, Inst Chem, State Key Lab Mol React Dynam, BNLMS, Beijing 100190, Peoples R China
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Yu, Youqing,Wu, Lidan,Zou, Xiaoran,et al. Time-Resolved and Mechanistic Study of the Photochemical Uncaging Reaction of the o-Hydroxycinnamic Caged Compound[J]. JOURNAL OF PHYSICAL CHEMISTRY A,2013,117(33):7767-7775.
APA Yu, Youqing,Wu, Lidan,Zou, Xiaoran,Dai, Xiaojuan,Liu, Kunhui,&Su, Hongmei.(2013).Time-Resolved and Mechanistic Study of the Photochemical Uncaging Reaction of the o-Hydroxycinnamic Caged Compound.JOURNAL OF PHYSICAL CHEMISTRY A,117(33),7767-7775.
MLA Yu, Youqing,et al."Time-Resolved and Mechanistic Study of the Photochemical Uncaging Reaction of the o-Hydroxycinnamic Caged Compound".JOURNAL OF PHYSICAL CHEMISTRY A 117.33(2013):7767-7775.
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