title: Radical C-H arylation of the BODIPY core with aryldiazonium salts: synthesis of highly fluorescent red-shifted dyes.
abstract: We describe herein the first radical C-H arylation of BODIPY dyes. This novel, general, one-step synthetic procedure uses ferrocene to generate aryl radical species from aryldiazonium salts and allows the straightforward synthesis of brightly fluorescent (Φ>0.85) 3,5-diarylated and 3-monoarylated boron dipyrrins in up to 86 % yield for a broad range of aryl substituents. In this way, new and complex dyes with red-shifted spectra can be easily prepared.
authors.affiliation: Molecular Design and Synthesis and Molecular Visualization and Photonics, Department of Chemistry, KU Leuven, Celestijnenlaan 200f-bus 02404, 3001 Leuven (Belgium).
authors.forename: Bram
authors.initials: B
authors.lastname: Verbelen
authors.forename: Stijn
authors.initials: S
authors.lastname: Boodts
authors.forename: Johan
authors.initials: J
authors.lastname: Hofkens
authors.forename: Noël
authors.initials: N
authors.lastname: Boens
authors.forename: Wim
authors.initials: W
authors.lastname: Dehaen
keywords: BODIPY; arylation; dyes; photophysics; radicals