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Photolabile coumarins with improved efficiency through azetidinyl substitution† †Electronic supplementary information (ESI) available: Experimental details, ESI figures and NMR spectra. See DOI: 10.1039/c7sc03627b

Authors :
Bassolino, Giovanni
Nançoz, Christoph
Thiel, Zacharias
Bois, Estelle
Vauthey, Eric
Rivera-Fuentes, Pablo
Source :
Chemical Science
Publication Year :
2017
Publisher :
Royal Society of Chemistry, 2017.

Abstract

The efficiency of photoactivatable coumarins in water has been enhanced by substitution with azetidine.<br />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.

Subjects

Subjects :
Chemistry

Details

Language :
English
ISSN :
20416539 and 20416520
Volume :
9
Issue :
2
Database :
OpenAIRE
Journal :
Chemical Science
Accession number :
edsair.pmid..........b80d8e9d29ad8652f7152d4067086e02