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dc.contributor.authorBąk, Krzysztof M. .
dc.contributor.authorChabuda, Krzysztof .
dc.contributor.authorMontes Andrés, Helena 
dc.contributor.authorQuesada Pato, Roberto 
dc.contributor.authorChmielewski, Michał J. .
dc.date.accessioned2018-08-24T08:25:20Z
dc.date.available2019-07-28T02:45:07Z
dc.date.issued2018-07
dc.identifier.issn1477-0520
dc.identifier.urihttp://hdl.handle.net/10259/4880
dc.description.abstractThe synthesis, structure and anion recognition properties of an extensive, rationally designed series of bisamide derivatives of 1,8-diaminocarbazole and 1,8-diamino-3,6-dichlorocarbazole are described. Despite simple structures and the presence of only three hydrogen bond donors, such compounds are remarkably strong and selective receptors for oxyanions in DMSO + 0.5%H2O. Owing to their carbazole fluorophore, they are also sensitive turn-on fluorescent sensors for H2PO4− and AcO−, with a more than 15-fold increase in fluorescence intensity upon binding. Despite relatively weak chloride affinity, some of the diamidocarbazoles have also been shown, for the first time, to be very active chloride transporters through lipid bilayers. The binding, sensing and transport properties of these receptors can be easily modulated by the usually overlooked variations in the length and degree of branching of their alkyl side arms. Overall, this study demonstrates that the 1,8-diamidocarbazole binding unit is a very promising and synthetically versatile platform for the development of fluorescent sensors and transporters for anions.en
dc.description.sponsorshipPolish National Science Centre for grant OPUS (2011/01/B/ST5/03900). The study was carried out at the Biological and Chemical Research Centre, University of Warsaw, established within a project co-financed by the European Union through the European Regional Development Fund under the Operational Programme Innovative Economy 2007–2013. R. Q. thanks financial support provided by Consejería de Educación – Junta de Castilla y León (Project BU092U16)en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherRoyal Society of Chemistryen
dc.relation.ispartofOrganic & Biomolecular Chemistry. 2018, V. 16, n. 28, p. 5188-5196en
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.title1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transportersen
dc.typeArtículoes
dc.typeinfo:eu-repo/semantics/article
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttps://doi.org/10.1039/C8OB01031E
dc.identifier.doi10.1039/C8OB01031E
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU092U16
dc.relation.projectIDinfo:eu-repo/grantAgreement/PolishNational ScienceCentre/2011-01-B-ST5-03900
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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