Nepomnyashchii Alexander B, Pistner Allen J, Bard Allen J, Rosenthal Joel
Department of Chemistry and Biochemistry, The University of Texas at Austin, Austin, Texas 78712.
J Phys Chem C Nanomater Interfaces. 2013 Mar 21;117(11):5599-5609. doi: 10.1021/jp312166w.
A set polyethylene glycol (PEG) appended BODIPY architectures () have been prepared and studied in CHCl, HO:CHCN (1:1) and aqueous solutions. and both contain a short PEG chain and differ in substitution about the BODIPY framework. is comprised of a fully substituted BODIPY moiety linked to a PEG polymer that is roughly 13 units in length. The photophysics and electrochemical properties of these compounds have been thoroughly characterized in CHCl and aqueous CHCN solutions. The behavior of correlates with established rules of BODIPY stability based on substitution about the BODIPY moiety. ECL for each of these compounds was also monitored. , which is unsubstituted at the 2- and 6-positions dimerized upon electrochemical oxidation while , which contains ethyl groups at the 2- and 6-positions, was much more robust and served as an excellent ECL luminophore. is highly soluble in water due to the long PEG tether and demonstrated modest ECL activity in aqueous solutions using tri-n-propylamine (TPrA) as a coreactant. As such, represents the first BODIPY derivative that has been shown to display ECL in water without the need for an organic cosolvent, and marks an important step in the development of BODIPY based ECL probes for various biosensing applications.
已经制备了一组连接有聚乙二醇（PEG）的BODIPY结构，并在CHCl、水：乙腈（1:1）和水溶液中进行了研究。 和 都含有一条短PEG链，并且在BODIPY骨架的取代情况上有所不同。 由一个完全取代的BODIPY部分与一个长度约为13个单元的PEG聚合物相连组成。这些化合物的光物理和电化学性质已在CHCl和乙腈水溶液中得到充分表征。 的行为与基于BODIPY部分取代的已确立的BODIPY稳定性规则相关。还监测了这些化合物各自的电化学发光（ECL）。在2-和6-位未取代的 在电化学氧化时二聚，而在2-和6-位含有乙基的 则更稳定，是一种优异的ECL发光体。由于长PEG链的存在， 高度溶于水，并在以三正丙胺（TPrA）作为共反应剂的水溶液中表现出适度的ECL活性。因此， 代表了第一种已被证明在水中无需有机共溶剂即可显示ECL的BODIPY衍生物，标志着基于BODIPY的ECL探针用于各种生物传感应用开发中的重要一步。
