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

页码：4213 / 4217

页数：5

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