Premium
Postfunctionalization of the BODIPY Core: Synthesis and Spectroscopy
Author(s) -
Boens Noël,
Verbelen Bram,
Dehaen Wim
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201500682
Subject(s) - bodipy , chemistry , nucleophile , pyrrole , combinatorial chemistry , nucleophilic substitution , ring (chemistry) , nucleophilic aromatic substitution , photochemistry , catalysis , oxidative coupling of methane , nitration , regioselectivity , medicinal chemistry , organic chemistry , fluorescence , physics , quantum mechanics
In this review we describe the various new methodologies for synthetic postmodification of the BODIPY core designed and developed by our research groups, as well as their electronic spectroscopic properties. We discuss the different strategies created for functionalization of the BODIPY framework at the pyrrole C‐ring positions and the meso ‐position. Halogenated boron dipyrrins are substrates for nucleophilic substitution or Pd‐catalyzed cross‐coupling reactions. α‐Unsubstituted BODIPYs can be functionalized with N and C nucleophiles through oxidative or vicarious nucleophilic substitution (VNS) of the α‐hydrogen atoms. Combining this methodology with reversible Michael addition onto nitrostyrenes provides a route to 3‐styrylated BODIPYs. Furthermore, the one‐step, Pd‐catalyzed C–H arylation of 3,5‐unsubstituted BODIPYs leads to 3‐ and 3,5‐arylated dyes. Finally, radical C–H arylation at the 3,5‐positions of α‐unsubstituted BODIPYs provides an additional synthesis route to arylated dyes.