Tetraphenylethylene- and fluorene-functionalized near-infrared aza-BODIPY dyes for living cell imaging
Tetraphenylethylene- and fluorene-functionalized near-infrared aza-BODIPY dyes for living cell imaging
复制标题
用于活细胞成像的四苯乙烯和芴功能化近红外氮杂-BODIPY 染料
DOI：
10.1039/c7ra10820f
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发表时间：
2017-01-01
期刊：
影响因子：
3.9
通讯作者：
Chen, Zhijian
中科院分区：
文献类型：
--
作者：
Zhu, Li;Xie, Wensheng;Chen, Zhijian
合成了4种含1,7位和3,5位四苯基取代基和芴基取代基的近红外（NIR）硼-氮杂二吡啶（aza-BODIPY）染料，并用H-1 NMR、C-13 NMR和HRMS对其进行了表征。用x射线晶体学研究了化合物5c的单晶结构。紫外/可见光谱和荧光光谱研究表明，与1,3,5,7-四苯基aza-BODIPY染料相比，这些染料的吸收和发射最大值在48 nm处发生了色移。此外，新染料的荧光量子产率高达0.45。用循环伏安法研究了这些染料的氧化还原性能。前沿分子轨道的DFT计算进一步阐明了所观察到的染料的光学和电化学性质。由于其优异的荧光特性，这些染料可以用作活细胞的荧光成像探针。
Four near-infrared (NIR) boron-azadipyrromethene (aza-BODIPY) dyes 5a-d bearing tetraphenylethylene- and fluorenyl substituents at the 1,7-position or 3,5-position were synthesized and characterized by H-1 NMR, C-13 NMR and HRMS. The single crystal structure of compound 5c was studied by X-ray crystallography. UV/vis and fluorescence spectroscopic studies of the aza-BODIPY dyes 5a-d indicated that the absorption and emission maxima of these dyes were bathochromically shifted up to 48 nm in comparison with that of the 1,3,5,7-tetraphenyl aza-BODIPY. Moreover, fluorescence quantum yields up to 0.45 were observed for the new dyes. The redox properties of these dyes were investigated by cyclic voltammetry. The observed optical and electrochemical properties of these dyes were further elucidated by the DFT calculation of the frontier molecular orbitals. Owing to their outstanding fluorescence properties, these dyes can be applied as fluorescence imaging probes for living cells.