Jump to main content
Jump to site search

Issue 25, 2019
Previous Article Next Article

Solvent-dependent photophysics of a red-shifted, biocompatible coumarin photocage

Author affiliations

Abstract

Controlling the activity of biomolecules with light-triggered photocages is an important research tool in the life sciences. We describe here a coumarin photocage that unusually combines the biocompatible optical properties of strong absorption at a long wavelength close to 500 nm and high photolysis quantum yields. The favourable properties are achieved by synthetically installing on the photocage scaffold a diethyl amino styryl moiety and a thionoester group rather than the lactone typical for coumarins. The photocage's photophysics are analysed with microsecond transient absorption spectroscopy to reveal the nature of the excited state in the photolysis pathway. The excited state is found to be strongly dependent on solvent polarity with a triplet state formed in DMSO and a charge-separated state in water that is likely due to aggregation. A long triplet lifetime is also correlated with a high photolysis quantum yield. Our study on the biocompatible photocage reveals fundamental insight for designing advanced photocages such as longer wavelengths in different solvent conditions tailored for applications in basic and applied research.

Graphical abstract: Solvent-dependent photophysics of a red-shifted, biocompatible coumarin photocage

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Mar 2019, accepted on 28 May 2019 and first published on 06 Jun 2019


Article type: Paper
DOI: 10.1039/C9OB00632J
Org. Biomol. Chem., 2019,17, 6178-6183
  • Open access: Creative Commons BY license
  •   Request permissions

    Solvent-dependent photophysics of a red-shifted, biocompatible coumarin photocage

    D. Offenbartl-Stiegert, T. M. Clarke, H. Bronstein, H. P. Nguyen and S. Howorka, Org. Biomol. Chem., 2019, 17, 6178
    DOI: 10.1039/C9OB00632J

    This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. Material from this article can be used in other publications provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC.
    • For reproduction of material from PCCP:
      [Original citation] - Published by the PCCP Owner Societies.
    • For reproduction of material from PPS:
      [Original citation] - Published by The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC.
    • For reproduction of material from all other RSC journals:
      [Original citation] - Published by The Royal Society of Chemistry.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements