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A pseudorotaxane formed from a cucurbit[7]uril wheel and a bioinspired molecular axle with pH, light and redox-responsive properties

2020-02Journal article Restricted access
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dc.contributor.authorSeco, André
dc.contributor.authorDiniz, Ana Marta
dc.contributor.authorSarrato, João
dc.contributor.authorMourão, Henrique
dc.contributor.authorCruz, Hugo
dc.contributor.authorParola, A. Jorge
dc.contributor.authorBasílio, Nuno
dc.date.accessioned2020-06-10T18:55:15Z
dc.date.available2020-06-10T18:55:15Z
dc.date.issued2020-02
dc.description.abstractA pH-, light- and redox-responsive flavylium-bipyridinium molecular dyad (bioinspired in natural anthocyanins) were synthesized and employed to devise a pseudorotaxane with the macrocycle cucurbit[7]uril (CB7) in aqueous solution. The inclusion complex was characterized by UV-Vis absorption, fluorescence emission, NMR, and electrochemical techniques which demonstrate the formation of a stable binary complex between the dyad and CB7 both under acidic and neutral conditions. It is noteworthy that the flavylium-bipyridinium tricationic dyad is only stable in highly acidic media, undergoing a reversible hydration reaction at slightly acidic or neutral pH to give a trans-chalcone-bipyridinium dication. 1H NMR experiments showed that in this last species the CB7 binds to the bipyridinium unit while in the tricationic species the macrocycle is positioned between the flavylium and the bipyridinium moieties. The different location of the CB7 wheel in the two dyad states allows control of the shuttling movement using light and pH stimuli that trigger the interconversion between these two species.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationSeco A, Diniz AM, Sarrato J, Mourão H, Cruz H, Parola AJ, et al. A pseudorotaxane formed from a cucurbit[7]uril wheel and a bioinspired molecular axle with pH, light and redox-responsive properties. Pure Appl Chem. 2020;92(2):301-13.pt_PT
dc.identifier.doi10.1515/pac-2019-0225pt_PT
dc.identifier.urihttp://hdl.handle.net/10400.21/11817
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.relation.publisherversionhttps://www.degruyter.com/view/journals/pac/92/2/article-p301.xmlpt_PT
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/pt_PT
dc.subjectFlavylium photoswitchespt_PT
dc.subjectMolecular machinespt_PT
dc.subjectNICE-2018pt_PT
dc.subjectPhotochemistrypt_PT
dc.subjectSupramolecular chemistrypt_PT
dc.titleA pseudorotaxane formed from a cucurbit[7]uril wheel and a bioinspired molecular axle with pH, light and redox-responsive propertiespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage313pt_PT
oaire.citation.issue2pt_PT
oaire.citation.startPage301pt_PT
oaire.citation.titlePure and Applied Chemistrypt_PT
oaire.citation.volume92pt_PT
person.familyNameDiniz
person.givenNameAna Marta Correia
person.identifierC-6705-2013
person.identifier.ciencia-id681D-28CE-8AF9
person.identifier.orcid0000-0003-3157-6937
rcaap.rightsrestrictedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication8b39e02b-0088-4d88-9267-3e6ffef55408
relation.isAuthorOfPublication.latestForDiscovery8b39e02b-0088-4d88-9267-3e6ffef55408

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