Issue 9, 2012
From the journal:

Photochemical & Photobiological Sciences

2-Hydroxyphenacyl ester: a new photoremovable protecting group†‡

Bokolombe Pitchou Ngoy,ab   Peter Šebej,ab   Tomáš Šolomek,ab   Bum Hee Lim,c   Tomáš Pastierik,a   Bong Ser Park,c   Richard S. Givens,d   Dominik Hegerab  and  Petr Klán*ab  

* Corresponding authors

a Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno, Czech Republic
E-mail: klan@sci.muni.cz
Fax: +420-54949-2443
Tel: +420-54949-4856

b Research Centre for Toxic Compounds in the Environment, Faculty of Science, Masaryk University, Kamenice 3, 625 00 Brno, Czech Republic

c Department of Chemistry, Dongguk University, Seoul 100-715, Korea

d Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, 5010 Malott Hall, 66045 Lawrence, KS, USA

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

DOI
https://doi.org/10.1039/C2PP25133G
Article type
Paper
Submitted
03 May 2012
Accepted
11 Jun 2012
First published
06 Jul 2012

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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