The design of novel benzoin acetate photolabile protecting groups

Photoremovable protecting groups are powerful tools for the release or deprotection of a wide range of molecules. Benzoin type photoremovable protecting groups are renowned for their exceptional properties but have been significantly underdeveloped. This thesis concerns the design, synthesis, and evaluation of four molecules in the benzoin class. A review of the benzoin photolabile protecting group is presented in Chapter 2. The first study, featured in Chapter 3, revisits the fundamental photochemistry of the 3',5'-dimethoxybenzoin acetate photolabile protecting group and explores that of two polyaromatic derivatives. In a second study, Chapter 4, the unique photochemistry of a donor acceptor 4-dimethylamino-3',5'-dimethoxybenzoin photocage is examined. The implications of the deviation of this photorelease from all known mechanistic pathways are discussed. A second donor-acceptor derivative 4-methoxy-3',5'-dimethoxybenzoin was designed to combine the traditional photochemistry of dimethoxybenzoin acetate with the advantageous properties of the previous donor acceptor species