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2-(1′-Hydroxyethyl)-anthraquinone as a photolabile protecting group for carboxylic acids

Paper ID Volume ID Publish Year Pages File Format Full-Text
27965 44053 2009 6 PDF Available
Title
2-(1′-Hydroxyethyl)-anthraquinone as a photolabile protecting group for carboxylic acids
Abstract

Using anthraquinone 2-yl ethyl (Aqe) as a photolabile protecting group for carboxylic acids, five caged compounds, Aqe esters of p-methoxybenzoic acid (1a), o-methylbenzoic acid (1b), benzoic acid (1c), p-nitrobenzoic acid (1d) and N-acetyl-l-tryptophan (1e), have been prepared, and their photochemistry was investigated. Upon 350 nm light irradiation, three caged compounds 1a–c in methanol solutions can efficiently release the corresponding carboxylic acids, their quantum yields ranging from 0.12 to 0.08. The intramolecular triplet–triplet energy transfer and the intramolecular electron transfer between triplet anthraquinone and the caged acids may occur, leading to a low efficiency of caged compounds 1d and 1e, respectively. Furthermore, based on quenching experiments, HPLC and spectral analysis, the mechanism of the uncaging reaction was suggested.

Keywords
Photolabile protecting groups; Carboxylic acids; Photochemistry
First Page Preview
2-(1′-Hydroxyethyl)-anthraquinone as a photolabile protecting group for carboxylic acids
Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 204, Issue 1, 30 April 2009, Pages 13–18
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering