Amphiphilic Near-IR-Emitting 3,5-Bis(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs
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2021-06-15
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Citation of Original Publication
Ansteatt, Sara; Meares, Adam; Ptaszek, Marcin; Amphiphilic Near-IR-Emitting 3,5-Bis(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs; The Journal of Organic Chemistry, 86, 13, 8755–8765, 15 June, 2021; https://doi.org/10.1021/acs.joc.1c00586
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This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.1c00586
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in The Journal of Organic Chemistry, copyright © American Chemical Society after peer review. To access the final edited and published work see https://pubs.acs.org/doi/10.1021/acs.joc.1c00586
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Abstract
A series of 3,5-bis(hetero)arylethenyl-substituted BODIPY derivatives have been prepared by Knoevenagel-type condensation of alkyl-substituted BODIPY with the corresponding aldehydes. 2-Pyrrolylethenyl-substituted derivatives feature near-IR emission (λₑₘ>700 nm) with a high fluorescence quantum yield. Both the emission maxima and fluorescence quantum yields are relatively insensitive to solvent polarity, contrary to the corresponding near-IR-emitting 4-(N,N-dimethylaminophenyl)ethenyl derivatives. Alkylation at the N-pyrrolic position of the ethenyl substituent allows for the installation of the hydrophilic PEG group and afforded amphiphilic BODIPY derivatives. Overall, 2-pyrrolylethenyl-substituted BODIPY derivatives appear to be versatile fluorophores with potential applications in near-IR imaging.