Radical CH Arylation of the BODIPY Core with Aryldiazonium Salts: Synthesis of Highly Fluorescent Red-Shifted Dyes

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...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2015-04, Vol.54 (15), p.4612-4616
Main Authors: Verbelen, Bram, Boodts, Stijn, Hofkens, Johan, Boens, Noël, Dehaen, Wim
Format: Article
Language:English
Subjects:
Aromatic compounds
arylation
BODIPY
Boron
Dyes
Ferrocenes
photophysics
Radicals
Spectra
Synthesis
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Summary: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. A one‐step procedure for the first radical CH arylation of BODIPY dyes has been developed. This method uses ferrocene [FeCp2] to generate aryl radical species from aryldiazonium salts and allows the 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201410853