2-Hydroxyphenacyl ester: a new photoremovable protecting group
|Year of publication
|Article in Periodical
|Magazine / Source
|Photochemical & Photobiological Sciences
|MU Faculty or unit
|Photochemistry; 2-Hydroxyphenacyl ester; photoremovable protecting group
|A 2-hydroxyphenacyl moiety absorbing below 370 nm is proposed as a new photoremovable protecting group for carboxylates and sulfonates. Laser flash photolysis and steady-state sensitization studies show that the leaving group is released from a short-lived triplet state. In addition, DFT-based quantum chemical calculations were performed to determine the key reaction steps. We found that triplet excited state intramolecular proton transfer represents a major deactivation channel. Minor productive pathways involving the triplet anion and quinoid triplet enol intermediates have also been identified.