Fluorogenic Sydnone-Modified Coumarins Switched-On by Copper-Free Click Chemistry

Autor:	Frédéric Friscourt, Camille Favre
Rok vydání:	2018
Předmět:	010405 organic chemistry Chemistry Organic Chemistry 010402 general chemistry Coumarin 01 natural sciences Biochemistry Fluorescence Combinatorial chemistry 0104 chemical sciences chemistry.chemical_compound Reagent Moiety Physical and Theoretical Chemistry Sydnone Copper-free click chemistry
Zdroj:	Organic Letters. 20:4213-4217
ISSN:	1523-7052 1523-7060
DOI:	10.1021/acs.orglett.8b01587
Popis:	The synthesis, photophysical characterization, and biochemical application of sydnone-modified coumarins, a novel class of fluorogenic clickable reagents, are reported. The sydnone moiety, a stable aromatic 1,3-dipole, efficiently quenched the fluorescence of coumarin, which could be restored, with a 132-fold enhancement, upon cycloadditions with cyclooctynes, thereby expanding the fluorogenic click toolbox. TD-DFT calculations suggest that the fluorescence quenching of the sydnone-modified coumarins is likely due to the presence of an energetically low-lying nonemissive charge-separated state.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::e5fc95cffb66fa677f3018975555b17f https://doi.org/10.1021/acs.orglett.8b01587 Zobrazit plný text záznamu