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Photolabile coumarins with improved efficiency through azetidinyl substitution.
Journal article

Photolabile coumarins with improved efficiency through azetidinyl substitution.

  • Bassolino G Laboratorium für Organische Chemie , ETH Zürich , HCI G329, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: pablo.rivera-fuentes@org.chem.ethz.ch.
  • Nançoz C Department of Physical Chemistry , University of Geneva , 30 Quai Ernest-Ansermet , 1211 Geneva 4 , Switzerland . Email: Eric.Vauthey@unige.ch.
  • Thiel Z Laboratorium für Organische Chemie , ETH Zürich , HCI G329, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: pablo.rivera-fuentes@org.chem.ethz.ch.
  • Bois E Department of Physical Chemistry , University of Geneva , 30 Quai Ernest-Ansermet , 1211 Geneva 4 , Switzerland . Email: Eric.Vauthey@unige.ch.
  • Vauthey E Department of Physical Chemistry , University of Geneva , 30 Quai Ernest-Ansermet , 1211 Geneva 4 , Switzerland . Email: Eric.Vauthey@unige.ch.
  • Rivera-Fuentes P Laboratorium für Organische Chemie , ETH Zürich , HCI G329, Vladimir-Prelog-Weg 3 , 8093 Zürich , Switzerland . Email: pablo.rivera-fuentes@org.chem.ethz.ch.
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  • 2018-04-10
Published in:
  • Chemical science. - 2018
English Azetidinyl substituents have been recently used to improve the fluorescence quantum yield of several classes of fluorophores. Herein, we demonstrate that other useful photochemical processes can be modulated using this strategy. In particular, we prepared and measured the quantum yield of photorelease of a series of 7-azetidinyl-4-methyl coumarin esters and compared it to their 7-diethylamino and julolidine-fused analogues. The efficiency of the photorelease reactions of the azetidinyl-substituted compounds was 2- to 5-fold higher than the corresponding diethylamino coumarins. We investigated the origin of this effect in model fluorophores and in the photoactivatable esters, and found that H-bonding with the solvent seems to be the prominent deactivation channel inhibited upon substitution with an azetidinyl ring. We anticipate that this substitution strategy could be used to modulate other photochemical processes with applications in chemical biology, catalysis and materials science.
Language
  • English
Open access status
gold
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Persistent URL
https://folia.unifr.ch/global/documents/78699
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