Photolabile coumarins with improved efficiency through azetidinyl substitution

Article Article scientifique Article Photolabile coumarins with improved efficiency through azetidinyl substitution eng 2018 author Bassolino Giovanni author Nancoz Christoph 670890 author Thiel Zacharias author Bois Estelle Marine 783174 author Vauthey Eric 0000-0002-9580-9683 133895 author Rivera-Fuentes Pablo 387-391 10.1039/C7SC03627B 2041-6520 http://xlink.rsc.org/?DOI=C7SC03627B 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. Dewey 540 Swiss National Science Foundation Applications de la spectroscopie ultrarapide à l'étude de processus photoinduits en phase condensée 165890 CH Project funding 38 Département de chimie physique 142 false 686 Groupe Vauthey Chemical Science 9 2 8d0425b6-7c07-49e0-9e81-b52590d5daa0 Article (Published version) Public BassolinoCS18.pdf 841325 application/pdf openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie physique

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Photolabile coumarins with improved efficiency through azetidinyl substitution	Chemical Science			2018	422	212

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