Amphiphilic Near-IR-Emitting 3,5-Bis(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs
| dc.contributor.author | Ansteatt, Sara | |
| dc.contributor.author | Meares, Adam | |
| dc.contributor.author | Ptaszek, Marcin | |
| dc.date.accessioned | 2021-07-06T14:31:37Z | |
| dc.date.available | 2021-07-06T14:31:37Z | |
| dc.date.issued | 2021-06-15 | |
| dc.description.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. | en_US |
| dc.description.sponsorship | This work was supported by the National Cancer Institute of the National Institutes of Health under Award Number U01CA181628. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health | en_US |
| dc.description.uri | https://pubs.acs.org/doi/10.1021/acs.joc.1c00586 | en_US |
| dc.format.extent | 32 pages | en_US |
| dc.genre | journal articles preprints | en_US |
| dc.identifier | doi:10.13016/m27zky-7txg | |
| dc.identifier.citation | 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 | en_US |
| dc.identifier.uri | https://doi.org/10.1021/acs.joc.1c00586 | |
| dc.identifier.uri | http://hdl.handle.net/11603/21856 | |
| dc.language.iso | en_US | en_US |
| dc.relation.isAvailableAt | The University of Maryland, Baltimore County (UMBC) | |
| dc.relation.ispartof | UMBC Chemistry & Biochemistry Department Collection | |
| dc.relation.ispartof | UMBC Faculty Collection | |
| dc.relation.ispartof | UMBC Student Collection | |
| dc.rights | This item is likely protected under Title 17 of the U.S. Copyright Law. Unless on a Creative Commons license, for uses protected by Copyright Law, contact the copyright holder or the author. | |
| dc.rights | 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 | |
| dc.title | Amphiphilic Near-IR-Emitting 3,5-Bis(2-Pyrrolylethenyl)BODIPY Derivatives: Synthesis, Characterization, and Comparison with Other (Hetero)Arylethenyl-Substituted BODIPYs | en_US |
| dc.type | Text | en_US |