Please use this identifier to cite or link to this item: http://hdl.handle.net/1822/33378

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dc.contributor.authorMarín-Hernández, Cristinapor
dc.contributor.authorSantos-Figueroa, Luis E.por
dc.contributor.authorMoragues, María E.por
dc.contributor.authorRaposo, M. Manuela M.por
dc.contributor.authorRosa M. F. Batistapor
dc.contributor.authorCosta, Susana P. G.por
dc.contributor.authorPardo,Teresapor
dc.contributor.authorMartínez-Máñez, Ramónpor
dc.contributor.authorSancenón, Félixpor
dc.date.accessioned2015-01-29T15:51:59Z-
dc.date.available2015-01-29T15:51:59Z-
dc.date.issued2014-
dc.date.submitted2014-
dc.identifier.citationJournal of Organic Chemistry, 79(22), 10752-10761. doi: 10.1021/jo501515epor
dc.identifier.issn0022-3263por
dc.identifier.issn1520-6904por
dc.identifier.urihttp://hdl.handle.net/1822/33378-
dc.description.abstractFour imidazo-anthraquinone derivatives (2a-d) functionalized with different aromatic and heteroaromatic groups were synthesized, characterized and their coordination behaviour against selected anions and cations tested. Acetonitrile solutions of probes 2a-d showed charge-transfer absorption bands in the 407-465 nm range whose positions depend on the electron donor strength of the (hetero)aromatic systems appended to the electron-acceptor anthraquinone group. The four probes were also emissive with fluorescence bands in the 533-571 nm interval. The recognition ability of 2a-d was evaluated in the presence of F-, Cl-, Br-, I-, OCN-, BzO-, ClO4-, AcO-, HSO4-, H2PO4- and CN-. Of all anions tested, only F-, AcO- and H2PO4- were able to induce the appearance of new red-shifted absorption bands in the probes that were ascribed to a deprotonation process involving the N-H moiety of the imidazole ring, especially when F- was used. Moreover addition of F-, AcO- and H2PO4- induced moderate quenching in the emission of 2a-d together with the appearance of a new red-shifted emission band. The UV-visible and emission behaviour of the four probes in the presence of Cu2+, Co2+, Mg2+, Fe3+, Ba2+, Fe2+, Ni2+, Ca2+, Zn2+, Pb2+, Cd2+, Cr3+, Al3+, K+ and Li+ was also assessed. Of all cations tested, only addition of the trivalent cations Fe3+, Cr3+ and Al3+ induced the appearance of a new blue-shifted emission in 2a-d that were ascribed to a preferential coordination of these metals with the acceptor part of the probes. Moreover trivalent cations induced an important quenching of the emission for 2a-d.por
dc.description.sponsorshipFundação para a Ciência e a Tecnologia (FCT)por
dc.language.isoengpor
dc.publisherAmerican Chemical Societypor
dc.rightsrestrictedAccesspor
dc.subjectsynthesispor
dc.subjectcolorimetric and fluorimetric chemosensorspor
dc.subjectbasic anionspor
dc.subjecttrivalent metal cationspor
dc.subjectimidazolespor
dc.subjectanthraquinonespor
dc.subjectthiophenepor
dc.subjectpyrrolepor
dc.subjectfuranpor
dc.subjectUV-visible spectroscopypor
dc.subjectfluorescencepor
dc.subjectchemosensorspor
dc.titleImidazo-anthraquinone derivatives for the chromo-fluorogenic sensing of basic anions and trivalent metal cationspor
dc.typearticlepor
dc.peerreviewedyespor
sdum.publicationstatuspublishedpor
oaire.citationStartPage10752por
oaire.citationEndPage10761por
oaire.citationIssue22por
oaire.citationTitleJournal of Organic Chemistrypor
oaire.citationVolume79por
dc.identifier.doi10.1021/jo501515epor
dc.identifier.pmid25365505por
dc.subject.fosCiências Naturais::Ciências Químicaspor
dc.subject.wosScience & Technologypor
sdum.journalJournal of Organic Chemistrypor
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