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Article: Acid-base controllable molecular shuttles

TitleAcid-base controllable molecular shuttles
Authors
Issue Date1998
Citation
Journal of the American Chemical Society, 1998, v. 120, n. 46, p. 11932-11942 How to Cite?
AbstractTwo novel [2]rotaxanes, comprised of a dibenzo[24]crown-8 (DB24C8) macroring bound mechanically to a chemical 'dumbbell' possessing two different recognition sites - viz., secondary dialkylammonium (NH2+) and 4,4'-bipyridinium (Bpym2+) units - have been synthesized by using the supramolecular assistance to synthesis provided by, inter alia, hydrogen bonding interactions. One of these rotaxanes bears a fluorescent and redox- active anthracene (Anth) stopper unit. NMR spectroscopy and X-ray crystallography have demonstrated that the DB24C8 macroring exhibits complete selectivity for the NH2+ recognition sites, i.e., that the [2]rotaxanes exist as only one of two possible translational isomers. Deprotonation of the rotaxanes' NH2+ centers effects a quantitative displacement of the DB24C8 macroring to the Bpym2+ recognition site, an outcome that can be reversed by acid treatment. The switching processes have been investigated by 1H NMR spectroscopy and, for the Anth-bearing rotaxane, by electrochemical and photophysical measurements. Furthermore, it is possible to drive the DB24C8 macroring from the dumbbell's Bpym2+ unit, in the deprotonated form of the Anth-bearing rotaxane, by destroying the stabilizing DB24C8-Bpym2+ charge- transfer interactions via electrochemical reduction. The photochemical and photophysical properties of this rotaxane (in both its protonated and deprotonated states) have also been investigated.
Persistent Identifierhttp://hdl.handle.net/10722/332442
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBallardini, Roberto-
dc.contributor.authorBalzani, Vincenzo-
dc.contributor.authorBaxter, Ian-
dc.contributor.authorCredi, Alberto-
dc.contributor.authorFyfe, Matthew C.T.-
dc.contributor.authorGandolfi, Maria Teresa-
dc.contributor.authorGómez-López, Marcos-
dc.contributor.authorMartínez-Díaz, M. Victoria-
dc.contributor.authorPiersanti, Arianna-
dc.contributor.authorSpencer, Neil-
dc.contributor.authorFraser Stoddart, J.-
dc.contributor.authorVenturi, Margherita-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:11:30Z-
dc.date.available2023-10-06T05:11:30Z-
dc.date.issued1998-
dc.identifier.citationJournal of the American Chemical Society, 1998, v. 120, n. 46, p. 11932-11942-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/332442-
dc.description.abstractTwo novel [2]rotaxanes, comprised of a dibenzo[24]crown-8 (DB24C8) macroring bound mechanically to a chemical 'dumbbell' possessing two different recognition sites - viz., secondary dialkylammonium (NH2+) and 4,4'-bipyridinium (Bpym2+) units - have been synthesized by using the supramolecular assistance to synthesis provided by, inter alia, hydrogen bonding interactions. One of these rotaxanes bears a fluorescent and redox- active anthracene (Anth) stopper unit. NMR spectroscopy and X-ray crystallography have demonstrated that the DB24C8 macroring exhibits complete selectivity for the NH2+ recognition sites, i.e., that the [2]rotaxanes exist as only one of two possible translational isomers. Deprotonation of the rotaxanes' NH2+ centers effects a quantitative displacement of the DB24C8 macroring to the Bpym2+ recognition site, an outcome that can be reversed by acid treatment. The switching processes have been investigated by 1H NMR spectroscopy and, for the Anth-bearing rotaxane, by electrochemical and photophysical measurements. Furthermore, it is possible to drive the DB24C8 macroring from the dumbbell's Bpym2+ unit, in the deprotonated form of the Anth-bearing rotaxane, by destroying the stabilizing DB24C8-Bpym2+ charge- transfer interactions via electrochemical reduction. The photochemical and photophysical properties of this rotaxane (in both its protonated and deprotonated states) have also been investigated.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleAcid-base controllable molecular shuttles-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja982167m-
dc.identifier.scopuseid_2-s2.0-0032567215-
dc.identifier.volume120-
dc.identifier.issue46-
dc.identifier.spage11932-
dc.identifier.epage11942-
dc.identifier.isiWOS:000077210900012-

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