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Radical CH Arylation of the BODIPY Core with Aryldiazonium Salts: Synthesis of Highly Fluorescent Red‐Shifted Dyes
Author(s) -
Verbelen Bram,
Boodts Stijn,
Hofkens Johan,
Boens Noël,
Dehaen Wim
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201410853
Subject(s) - bodipy , fluorescence , chemistry , aryl , ferrocene , boron , yield (engineering) , combinatorial chemistry , photochemistry , organic chemistry , materials science , electrochemistry , alkyl , physics , electrode , quantum mechanics , metallurgy
We describe herein the first radical CH 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.