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Pd-Catalyzed Direct C–H Functionalization/Annulation of BODIPYs with Alkynes to Access Unsymmetrical Benzo[b]-Fused BODIPYs: Discovery of Lysosome-Targeted Turn-On Fluorescent Probes
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2018-07-06 00:00:00 , DOI: 10.1021/acs.joc.8b01239
Xiuguang Yang 1 , Linfeng Jiang 1 , Mufan Yang 1 , Huaxing Zhang 1 , Jingbo Lan 1 , Fulin Zhou 1 , Xingyu Chen 1 , Di Wu 1 , Jingsong You 1
Affiliation  

A highly efficient palladium-catalyzed direct C–H functionalization/annulation of BODIPYs with alkynes has been developed for the first time to construct a series of unsymmetrical benzo[b]-fused BODIPYs from readily available starting materials. These unsymmetrical benzo[b]-fused BODIPYs exhibit remarkably red-shifted emissions and larger Stokes shifts than classical BODIPY dyes. Cell imaging experiments and cytotoxicity assays demonstrate that BODIPYs 4c and 4d have specific lysosome-labeling capacities, turn-on fluorescence emissions in cells, and low cytotoxicity.

中文翻译:

Pd催化的直接C–H功能化/带有炔烃的BODIPY环化以访问不对称的苯并[ b ]融合的BODIPY:溶酶体靶向的开启荧光探针的发现

首次开发了一种高效的钯催化的带有炔烃的BODIPY的直接C–H官能化/环化反应,用于从易于获得的起始原料中构建一系列不对称的苯并[ b ]稠合的BODIPY。这些不对称的苯并[ b ]稠合的BODIPY与传统的BODIPY染料相比,具有明显的红移发射和更大的斯托克斯位移。细胞成像实验和细胞毒性试验表明,BODIPYs 4c4d具有特异性的溶酶体标记能力,细胞中的开启荧光发射和低细胞毒性。
更新日期:2018-07-06
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