2-Hydroxyphenacyl ester: a new 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.

DOI: 10.1039/c2pp25133g

Cite this paper

@article{Ngoy20122HydroxyphenacylEA, title={2-Hydroxyphenacyl ester: a new photoremovable protecting group.}, author={Bokolombe Pitchou Ngoy and Peter Sebej and Tom{\'a}{\vs} {\vS}olomek and Bum Lim and Tom{\'a}{\vs} Pastierik and Bong Ser Park and Richard S Givens and Dominik Heger and Petr Kl{\'a}n}, journal={Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology}, year={2012}, volume={11 9}, pages={1465-75} }