Masking and demasking strategies for the BF2-BODIPYs as a tool for BODIPY fluorophores.
An efficient and chemoselective route for transforming BF2-BODIPYs to Et2B-BODIPYs (masking) was developed using Et2AlCl. The Et groups can be easily replaced with F atoms using BF3·Et2O in moist CH2Cl2 to regenerate the BF2-BODIPYs (demasking). The masking-demasking strategy is very useful for synthesizing functionalized BODIPYs via nucleophilic and reductive reactions. The masking strategy was used to synthesize a BODIPY dimer by McMurry coupling of a formyl Et2B-BODIPY, while a new BODIPY with an asymmetrically substituted B-center was synthesized using the demasking strategy.
Department of Dyestuff Technology, Institute of Chemical Technology , Mumbai 400019, India.
Ankush B
AB
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Soumyaditya
S
Mula
Shrikant
S
Thakare
Nagaiyan
N
Sekar
Alok K
AK
Ray
Subrata
S
Chattopadhyay
D001896:Boron Compounds / Q000737:chemistry*; D018360:Crystallography, X-Ray; D005456:Fluorescent Dyes / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes