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

被引：46
|
作者：
Favre, Camille [1 ,2 ]
Friscourt, Frederic [1 ,2 ]
机构：
[1] Univ Bordeaux, Inst Europeen Chim & Biol, 2 Rue Robert Escarpit, F-33607 Pessac, France
[2] CNRS UMR5287, Inst Neurosci Cognit & Integrat Aquitaine, Bordeaux, France
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 14期
关键词：
PROBES; FLUORESCENCE; LIGATION; EMISSION;
D O I：
10.1021/acs.orglett.8b01587
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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.
引用
收藏
页码：4213 / 4217
页数：5
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