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Issue 36, 2011
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UV-induced fluorescence recovery and solubility modulation of photocaged conjugated oligomers

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Abstract

This article describes photoactivatable conjugated oligomers that show both increased fluorescence quantum yield and pH-dependant solubility upon irradiation with UV light. Sonogashira coupling between ester-substituted phenylacetylenes and alkoxy-substituted diiodo phenylene-vinylenes yielded conjugated phenylene-ethynylene/phenylene-vinylene oligomers. Oligomers with nitrobenzyl ester moieties had quenched fluorescence in polar solvents; UV irradiation restored their quantum yield of fluorescence to that of corresponding alkyl ester-substituted oligomers. These photocaged oligomers also exhibited UV-induced changes in solubility consistent with photogeneration of carboxylic acids. This approach is therefore effective at tuning the properties of conjugated organics with light after traditional synthetic operations, and has potential for use in photoactivatable fluorophores or solution-processable multilayer devices.

Graphical abstract: UV-induced fluorescence recovery and solubility modulation of photocaged conjugated oligomers

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Publication details

The article was received on 03 Jun 2011, accepted on 20 Jul 2011, published on 10 Aug 2011 and first published online on 10 Aug 2011


Article type: Paper
DOI: 10.1039/C1JM12542G
Citation: J. Mater. Chem., 2011,21, 14041-14047
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    UV-induced fluorescence recovery and solubility modulation of photocaged conjugated oligomers

    R. H. Pawle, V. Eastman and S. W. Thomas, J. Mater. Chem., 2011, 21, 14041
    DOI: 10.1039/C1JM12542G

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