The photochemistry of acetyl-substituted aroyl azides: the design of photolabeling agents for inert sites in hydrophobic regions.

The photochemistry, photophysics and hydrolytic stability of three substituted aroyl azides were investigated. The azides were selected as model compounds for potential photolabeling agents based on the extreme electrophilic reactivity of aroylnitrenes. Each of the azides studied is a derivative of benzoyl azide containing an acyl group to act as an internal triplet sensitizer and an additional functional group useful for linking the azide to a site-selecting probe molecule. The findings show that benzoyl azides containing the three substituents in a 1,3,5-pattern might be useful for labeling of lipophilic molecules.