Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 24, Pages 9988-9996Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201754m
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Funding
- National Nature Science Foundation of China [20802002, 20902004, 21072005]
- Anhui Province [090416221, KJ2009A130]
- Ministry of Education of China [20093424120001]
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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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