Regioselective Stepwise Bromination of Boron Dipyrromethene (BODIPY) Dyes

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• 作者：Lijuan Jiao ; Weidong Pang ; Jinyuan Zhou ; Yun Wei ; Xiaolong Mu ; Guifeng Bai ; Erhong Hao
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：December 16, 2011
• 年：2011
• 卷：76
• 期：24
• 页码：9988-9996
• 全文大小：539K
• 年卷期：v.76,no.24(December 16, 2011)
• ISSN：1520-6904

文摘

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.