Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry , Sichuan University , 29 Wangjiang Road , Chengdu 610064 , P.R. China.
J Org Chem. 2018 Aug 17;83(16):9538-9546. doi: 10.1021/acs.joc.8b01239. Epub 2018 Jul 17.
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.
首次发展了一种高效的钯催化 BODIPYs 与炔烃的直接 C-H 官能化/环化反应，从易得的起始原料构建了一系列不对称苯并[ b]-稠合 BODIPYs。这些不对称苯并[ b]-稠合 BODIPYs 表现出比经典 BODIPY 染料显著红移的发射和更大的斯托克斯位移。细胞成像实验和细胞毒性测定表明，BODIPYs 4c 和 4d 具有特定的溶酶体标记能力，在细胞中开启荧光发射，且细胞毒性低。
