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Photochemical Reaction of Benzoin Caged Compound:Time-Resolved Fourier Transform Infrared Spectroscopy Study
Xiao-juan Dai,You-qing Yu,Kun-hui Liu,Hong-mei Su
Author NameAffiliationE-mail
Xiao-juan Dai Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China  
You-qing Yu Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China  
Kun-hui Liu College of Chemistry, Beijing Normal University, Beijing 100875, China kunhui@bnu.edu.cn 
Hong-mei Su Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;College of Chemistry, Beijing Normal University, Beijing 100875, China hongmei@iccas.ac.cn 
Abstract:
The benzoin group caged compound has received strong interests due to its excellent photo-deprotection properties and wide use in chemical and biological studies. We used time-resolved infrared spectroscopy to investigate the photochemical reaction of the benzoin caged compound, o-(2-methylbenzoyl)-DL-benzoin under 266 nm laser irradiation. Taking advantage of the specific vibrational marker bands and the IR discerning capability, we have detected and identified the uncaging product 2-methylbenzoic acid, and two intermediate radicals of benzoyl and 2-methylbenzoate benzyl in the transient infrared spectra. Our results provide spectral evidence to support the homolytic cleavage reaction of C-C=O bond in competition with the deprotection reaction. Moreover, the product yields of 2-methylbenzoic} acid and benzoyl radical were observed to be affected by solvents and a largely water containing solvent can be in favor of the deprotection reaction.
Key words:  Benzoin  Caged compound  Photo-deprotection  Time-resolved infrared spectroscopy
FundProject:
安息香笼化合物光化学反应的时间分辨红外光谱
代小娟,余友清,刘坤辉,苏红梅
摘要:
采用时间分辨红外吸收光谱方法,研究了邻甲基苯甲酸安息香酯在266 nm激光作用下发生的光化学反应,并考察了溶剂对反应过程的影响. 从瞬态红外光谱上观察到了邻甲基苯甲酸和苯甲酰自由基及苯偶酰,提供了直接的光谱证据证明了脱保护反应及C-C=O处均裂反应的发生. 通过对比溶剂中不同水含量下均裂反应中间体及邻甲基苯甲酸的产率,发现水含量在溶剂中的增加能促进脱保护反应的发生.
关键词:  安息香  笼化合物  光致脱保护反应  时间分辨红外吸收光谱
DOI:10.1063/1674-0068/29/cjcp1512260
分类号: