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Issue 9, 2012
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2-Hydroxyphenacyl ester: a new photoremovable protecting group

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Abstract

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.

Graphical abstract: 2-Hydroxyphenacyl ester: a new photoremovable protecting group

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Article information


Submitted
03 May 2012
Accepted
11 Jun 2012
First published
06 Jul 2012

Photochem. Photobiol. Sci., 2012,11, 1465-1475
Article type
Paper

2-Hydroxyphenacyl ester: a new photoremovable protecting group

B. P. Ngoy, P. Šebej, T. Šolomek, B. H. Lim, T. Pastierik, B. S. Park, R. S. Givens, D. Heger and P. Klán, Photochem. Photobiol. Sci., 2012, 11, 1465
DOI: 10.1039/C2PP25133G

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