连接各种外围取代基的四噻吩基功能化的吸收红色和近红外光的BODIPY染料。
Tetrathienyl-functionalized red- and NIR-absorbing BODIPY dyes appending various peripheral substituents.
作者信息
Liu Ping, Gao Feng, Zhou Lina, Chen Yu, Chen Zhijian
机构信息
School of Chemical Engineering and Technology, Tianjin University, Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 300072, China.
Department of Chemistry, School of Sciences, Tianjin University, China.
出版信息
Org Biomol Chem. 2017 Feb 7;15(6):1393-1399. doi: 10.1039/c6ob02612e.
A series of boron-dipyrromethene dyes (BODIPYs) 4a-g with different thienyl moieties at 2,3,5,6-positions of the BODIPY core were synthesized by the Stille cross-coupling reaction. The new compounds were characterized by H NMR, C NMR, HRMS, and IR spectroscopy. The single crystal structure of compound 4e was obtained by X-ray crystallography. The optical and electrochemical properties of these dyes were studied by UV/Vis spectroscopy, fluorescence spectroscopy, and cyclic voltammetry. The DFT calculation of the frontier molecular orbitals of these dyes corroborates the observed effects of peripheral substituents on the optical and redox properties. These results reveal a good tunability of the optical and electronic properties of these BODIPYs by varying the peripheral groups at the α-positions of thienyl moieties, which leads to the absorption and emission reaching the NIR region.
通过Stille交叉偶联反应合成了一系列在硼二吡咯亚甲基（BODIPY）核心的2,3,5,6位带有不同噻吩基部分的硼二吡咯亚甲基染料（BODIPYs）4a - g。通过¹H NMR、¹³C NMR、高分辨质谱（HRMS）和红外光谱对新化合物进行了表征。通过X射线晶体学获得了化合物4e的单晶结构。通过紫外/可见光谱、荧光光谱和循环伏安法研究了这些染料的光学和电化学性质。这些染料前沿分子轨道的密度泛函理论（DFT）计算证实了观察到的外围取代基对光学和氧化还原性质的影响。这些结果表明，通过改变噻吩基部分α位的外围基团，可以很好地调节这些BODIPYs的光学和电子性质，从而使吸收和发射达到近红外区域。
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