Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes
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硼二吡咯亚甲基 (BODIPY) 染料的区域选择性逐步溴化
DOI：
10.1021/jo201754m
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发表时间：
2011-12-16
影响因子：
3.6
通讯作者：
Hao, Erhong
中科院分区：
文献类型：
--
作者：
Jiao, Lijuan;Pang, Weidong;Hao, Erhong
卤代BODIPY是重要的合成前体和潜在的光动力学治疗（PDT）的敏化剂。使用溴的吡咯未取代的BODIPY的亲电溴化以良好至优异的产率以逐步方式区域选择性地产生单溴至七溴BODIPY。将这些所得溴代BODIPY用于区域选择性取代和Suzuki偶联反应，以良好至优异的产率生成BODIPY 4、5、6和7。根据NMR和X-射线分析结果，逐步溴化首先发生在2，6-位，然后在3，5-位，最后在1，7-位，而区域选择性取代首先发生在3，5-位，然后在1，7-位的发色团。研究了它们的光谱性质，结果表明，这些溴代BODIPY作为PDT敏化剂具有潜在的应用前景。
Halogenated BODIPYs are important synthetic precursors and potential sensitizers for photodynamic therapy (PDT). Electrophilic bromination of pyrrolic-unsubstituted BODIPYs using bromine regioselectively generated mono- to heptabromoBODIPYs in a stepwise fashion in good to excellent yields. These resultant bromoBODIPYs were applied for regioselective substitution and Suzuki coupling reaction to generate BODIPYs 4, 5, 6, and 7 in good to excellent yields. According to NMR and X-ray analysis results, the stepwise bromination first takes place at 2,6-, then at 3,5-, and eventually at 1,7-positions, whereas the regioselective substitution occurs first at 3,5- then at 1,7-positions of the chromophore. The spectroscopic properties of these resultant BODIPYs were studied, which shows the potential application of these bromoBODIPYs as sensitizers for PDT.