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An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease

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Abstract

Conjugates of a triplet sensitiser (a 4,4′-dialkoxybenzophenone) with 1-acetyl-7-nitroindolines show up to 20-fold enhancement for photorelease of acetate (relative to the same indolines lacking the attached sensitiser) upon irradiation at 300 nm in neutral aqueous solution. The sensitised photolysis can be carried out in the presence of dissolved oxygen and will be applicable to photorelease of other carboxylates. The enhanced efficiency is mediated by an antenna function of the sensitiser, which transfers its triplet energy to populate the reactive, short-lived triplet state of the acylnitroindoline. This energy transfer is confirmed by a large reduction of the sensitiser’s triplet lifetime in the conjugates compared with that of the sensitiser alone.

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Authors and Affiliations

  1. National Institute for Medical Research, The Ridgeway, Mill Hill, London, UK, NW7 1AA

    George Papageorgiou & John E. T. Corrie

  2. Department of Chemistry, University of Victoria, Box 3065, Victoria, British Columbia, Canada, V8W 3V6

    Matthew Lukeman & Peter Wan

Authors
  1. George Papageorgiou
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  2. Matthew Lukeman
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  3. Peter Wan
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  4. John E. T. Corrie
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Corresponding author

Correspondence to John E. T. Corrie.

Additional information

Electronic supplementary information (ESI) available: Synthetic details for starting materials and photolysis protocols for 4 plus the calculated absorption spectrum for 4, spectra of its progressive photolysis and comparisons of calculated and experimental absorption spectra for 4 and 5. See http://www.rsc.org/suppdata/pp/b3/b316251f/

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Papageorgiou, G., Lukeman, M., Wan, P. et al. An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease. Photochem Photobiol Sci 3, 366–373 (2004). https://doi.org/10.1039/b316251f

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  • DOI: https://doi.org/10.1039/b316251f

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