Amphiphilic Near-IR-Emitting 3,5-<i>Bis</i>(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs

A series of 3,5-bis(hetero)arylethenyl-substituted BODIPY derivatives have been prepared by Knoevenagel-type condensation alkyl-substituted with the corresponding aldehydes. 2-Pyrrolylethenyl-substituted feature near-IR emission (?em > 700 nm) a high fluorescence quantum yield. Both maxima and yields are relatively insensitive to solvent polarity, contrary near-IR-emitting 4-(N,N-dimethylaminophenyl)ethenyl derivatives. Alkylation at N-pyrrolic position ethenyl substituent allows for installation hydrophilic PEG group afforded amphiphilic Overall, 2-pyrrolylethenyl-substituted appear be versatile fluorophores potential applications in imaging.