Regioselective stepwise bromination of boron dipyrromethene (BODIPY) dyes |
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Authors: | Jiao Lijuan Pang Weidong Zhou Jinyuan Wei Yun Mu Xiaolong Bai Guifeng Hao Erhong |
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Institution: | Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui, 241000, China. jiao421@mail.ahnu.edu.cn |
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Abstract: | 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. |
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