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Article: A water-soluble pH-triggered molecular switch

TitleA water-soluble pH-triggered molecular switch
Authors
Issue Date2013
Citation
Journal of the American Chemical Society, 2013, v. 135, n. 47, p. 17691-17694 How to Cite?
AbstractA bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch. © 2013 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/333055
ISSN
2023 Impact Factor: 14.4
2023 SCImago Journal Rankings: 5.489
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorGrunder, Sergio-
dc.contributor.authorMcGrier, Psaras L.-
dc.contributor.authorWhalley, Adam C.-
dc.contributor.authorBoyle, Megan M.-
dc.contributor.authorStern, Charlotte-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:16:24Z-
dc.date.available2023-10-06T05:16:24Z-
dc.date.issued2013-
dc.identifier.citationJournal of the American Chemical Society, 2013, v. 135, n. 47, p. 17691-17694-
dc.identifier.issn0002-7863-
dc.identifier.urihttp://hdl.handle.net/10722/333055-
dc.description.abstractA bistable donor-acceptor [2]catenane, which is composed of a crown ether containing a hydroquinone unit and a 1,5-diaminonaphthalene unit, interlocked mechanically by cyclobis(paraquat-p-phenylene) as its tetrachloride, exists as a mixture of translational isomers, both in the solid state and in aqueous solution. UV/vis and 1H NMR spectroscopies demonstrate that this isomeric mixture can be switched in water in the presence of hydrochloric acid to afford a single diprotonated derivative in which only the hydroquinone unit resides inside the cavity of the tetracationic cyclophane. Treatment with 1,4-diazabicyclo[2.2.2]octane resets the molecular switch. © 2013 American Chemical Society.-
dc.languageeng-
dc.relation.ispartofJournal of the American Chemical Society-
dc.titleA water-soluble pH-triggered molecular switch-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ja409006y-
dc.identifier.scopuseid_2-s2.0-84889256696-
dc.identifier.volume135-
dc.identifier.issue47-
dc.identifier.spage17691-
dc.identifier.epage17694-
dc.identifier.eissn1520-5126-
dc.identifier.isiWOS:000328099400010-

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