Photoremovable protecting groups (PRPGs) are a class of photoreactive species that have the ability to release their protected moiety upon irradiation. PRPGs have potential use in many applications such as fragrance delivery in household goods and drug delivery. We designed a new PRPG, o-azidomethylacetophenone derivative that release their protected alcohol upon irradiation. The photorelease is initiated by intramolecular H atom abstraction to form a biradical that rearranges further. The mechanism for the photorelease was studied using laser flash photolysis, matrix isolation, and product studies. The proposed mechanism was further supported by density functional theory calculations.

Flexible photoremovable protecting groups (PRPGs) for efficient photorelease

251st National Meeting (2016)

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