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Highly sensitive and selective fluorescent probes for Cu(II) detection based on calix[4]arene-oxacyclophane architectures

2020-05-02Journal article Open access
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dc.contributor.authorCosta, Alexandra I.
dc.contributor.authorBarata, Patrícia
dc.contributor.authorFialho, Carina
dc.contributor.authorPrata, José V.
dc.date.accessioned2020-06-05T13:39:43Z
dc.date.available2020-06-05T13:39:43Z
dc.date.issued2020-05-02
dc.descriptionEste trabalho foi financiado pelo Concurso Anual para Projetos de Investigação, Desenvolvimento, Inovação e Criação Artística (IDI&CA) 2016 do Instituto Politécnico de Lisboa. Código de referência IPL/2016/NoSeMeTox_ISEL
dc.description.abstractA new topological design of fluorescent probes for sensing copper ion is disclosed. The calix[4]arene-oxacyclophane (Calix-OCP) receptor, either wired-in-series in arylene-alt-ethynylene conjugated polymers or standing alone as a sole molecular probe, display a remarkable a_nity and selectivity for Cu(II). The unique recognition properties of Calix-OCP system toward copper cation stem from its pre-organised cyclic array of O-ligands at the calixarene narrow rim, which is kept in a conformational rigid arrangement by a tethered oxacyclophane sub-unit. The magnitude of the binding constants (Ka = 5.30 􀀀 8.52 _ 104 M􀀀1) and the free energy changes for the inclusion complexation (􀀀DG = 27.0 􀀀 28.1 kJmol􀀀1), retrieved from fluorimetric titration experiments, revealed a high sensitivity of Calix-OCP architectures for Cu(II) species. Formation of supramolecular inclusion complexes was evidenced from UV-Vis spectroscopy. The new Calix-OCP-conjugated polymers (polymers 4 and 5), synthesized in good yields by Sonogashira–Hagihara methodologies, exhibit high fluorescence quantum yields (_F = 0.59 􀀀 0.65). Density functional theory (DFT) calculations were used to support the experimental findings. The fluorescence on–o_ behaviour of the sensing systems is tentatively explained by a photoinduced electron transfer mechanism.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationCOSTA, Alexandra I.; [et al] – Highly sensitive and selective fluorescent probes for Cu(II) detection based on calix[4]arene-oxacyclophane architectures. Molecules. ISSN 1420-3049. Vol. 25, N.º 10 (2020), pp. 1-17pt_PT
dc.identifier.doi10.3390/molecules25102456pt_PT
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.21/11780
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationUIDB/00616/2020 - FCT/MCTESpt_PT
dc.relationUIDP/00616/2020 - FCT/MCTESpt_PT
dc.relationProjeto financiado no âmbito do Concurso de Projetos de Investigação, Desenvolvimento, Inovação & Criação Artística (IDI&CA) financiados pelo Instituto Politécnico de Lisboa. IPL/2016/NoSeMeTox_ISELpt_PT
dc.subjectcalix[4]arenept_PT
dc.subjectcopperpt_PT
dc.subjectsupramolecularpt_PT
dc.subjectinclusion complexpt_PT
dc.subjectfluorescencept_PT
dc.subjectsensorpt_PT
dc.subjectdensity functional theorypt_PT
dc.titleHighly sensitive and selective fluorescent probes for Cu(II) detection based on calix[4]arene-oxacyclophane architecturespt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage17pt_PT
oaire.citation.issue10pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume25pt_PT
person.familyNameCosta
person.familyNameBarata
person.familyNameBento Fialho
person.familyNamePrata
person.givenNameAlexandra
person.givenNamePatrícia
person.givenNameCarina
person.givenNameJosé Virgílio
person.identifier1090399
person.identifier191765
person.identifier.ciencia-id4212-F7BF-D971
person.identifier.ciencia-idC019-9F30-0F99
person.identifier.ciencia-idD019-35D8-74CC
person.identifier.ciencia-idC11A-9130-8981
person.identifier.orcid0000-0002-5518-6506
person.identifier.orcid0000-0001-8274-633X
person.identifier.orcid0000-0003-3529-2069
person.identifier.orcid0000-0002-9068-2847
person.identifier.ridB-7214-2008
person.identifier.scopus-author-id8968446100
person.identifier.scopus-author-id8968446000
person.identifier.scopus-author-id9276778400
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
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relation.isAuthorOfPublication4ab8a01f-c11d-4b3b-b0cf-b21e5b634170
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relation.isAuthorOfPublication15e229f3-a619-4931-87eb-799091dc1601
relation.isAuthorOfPublication.latestForDiscovery15e229f3-a619-4931-87eb-799091dc1601

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