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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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Publication details

The article was received on 03 May 2012, accepted on 11 Jun 2012 and first published on 06 Jul 2012


Article type: Paper
DOI: 10.1039/C2PP25133G
Citation: Photochem. Photobiol. Sci., 2012,11, 1465-1475
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    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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