Issue 2, 2018

Photolabile coumarins with improved efficiency through azetidinyl substitution


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.

Graphical abstract: Photolabile coumarins with improved efficiency through azetidinyl substitution

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Article information

Article type
Edge Article
18 Aug 2017
31 Oct 2017
First published
31 Oct 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 387-391

Photolabile coumarins with improved efficiency through azetidinyl substitution

G. Bassolino, C. Nançoz, Z. Thiel, E. Bois, E. Vauthey and P. Rivera-Fuentes, Chem. Sci., 2018, 9, 387 DOI: 10.1039/C7SC03627B

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