Photochemical Reaction of Benzoin Caged Compound:Time-Resolved Fourier Transform Infrared Spectroscopy Study

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.