8-Functionalization of alkyl-substituted-3,8-dimethyl BODIPYs by Knoevenagel condensation.
New 8-alkenylBODIPYs have been synthesized by Knoevenagel condensation between a series of alkyl-substituted-3,8-dimethylBODIPYs and aromatic or aliphatic aldehydes. This is in clear contrast with literature precedents, which indicate that this reaction occurs exclusively on the methyl group at C-3. The change in hybridization of the carbon at the 8-position (from sp(3) to sp(2)) determines the fluorescence emission of the BODIPY, while the presence of electron-donating or -withdrawing groups leads to intramolecular charge transfer processes.
Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense, 28040 Madrid, Spain.
Eduardo
E
Palao
Antonia R
AR
Agarrabeitia
Jorge
J
Bañuelos-Prieto
Teresa Arbeloa
TA
Lopez
Iñigo
I
Lopez-Arbeloa
Diego
D
Armesto
Maria J
MJ
Ortiz