Boron dipyrromethenes (BODIPYs) are highly efficient fluorophores with a multitude of applications including but not limited to cell imaging and dye sensitized solar cells (DSSCs). A limitation in the future development of the functionalised BODIPYs is the need to develop novel reaction chemistry at the more challenging 3,5-positions. We have synthesized a range 3,5-dihalo BODIPYs, and shown that they are excellent synthetic intermediates for subsequent downstream functionalisation reactions. We have developed a synthesis of 3,5-dichloro BODIPYs using copper mediated oxidative nucleophilic substitution of hydrogen (ONSH) with chloride. Whereas 3,5-dibromo BODIPYs are synthesized via an electrophilic bromination of the precursor dipyrromethane, followed by subsequent oxidation and chelation to access the desired BODIPYs. To access previously unknown 3,5-diiodo BODIPYs, starting with the corresponding 3,5-dichloro and 3,5-dibromo BODIPYs, we have developed a high yielding, concerted aromatic Finkelstein reaction with NaI refluxing in propionitrile. We have also compared the use of 3,5-dichloro, dibromo and diiodo BODIPYs in a range of downstream functionalisation reactions including SNAr and palladium cross-couplings (Migita-Kosugi-Stille, Mizoroki-Heck, Sonogashira and Suzuki-Miyaura), showing in particular that 3,5-diiodo BODIPYs are excellent substrates for further development of the BODIPY dyes.

Synthesis of 3,5-dihalo boron dipyrromethenes (BODIPYs) and applications in concerted aromatic Finkelstein, SNAr and palladium cross-coupling reactions

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