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Fluorescent bis-calix[4]arene-carbazole conjugates: synthesis and inclusion complexation studies with fullerenes C-60 and C-70

2021-08-18Journal article Open access
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dc.contributor.authorBarata, Patrícia
dc.contributor.authorCosta, Alexandra I.
dc.contributor.authorCosta, Sérgio
dc.contributor.authorPrata, José V.
dc.date.accessioned2021-09-20T07:33:10Z
dc.date.available2021-09-20T07:33:10Z
dc.date.issued2021-08-18
dc.description.abstractSupramolecular chemistry has become a central theme in chemical and biological sciences over the last decades. Supramolecular structures are being increasingly used in biomedical applications, particularly in devices requiring specific stimuli-responsiveness. Fullerenes, and supramolecular assemblies thereof, have gained great visibility in biomedical sciences and engineering. Sensitive and selective methods are required for the study of their inclusion in complexes in various application fields. With this in mind, two new fluorescent bis-calix[4]arene-carbazole conjugates (4 and 5) have been designed. Herein, their synthesis and ability to behave as specific hosts for fullerenes C-60 and C-70 is described. The optical properties of the novel compounds and their complexes with C-60 and C-70 were thoroughly studied by UV-Vis and steady-state and time-resolved fluorescence spectroscopies. The association constants (K-a) for the complexation of C-60 and C-70 by 4 and 5 were determined by fluorescence techniques. A higher stability was found for the C-70@4 supramolecule (K-a = 5.6 x 10(4) M-1; Delta G = -6.48 kcal/mol). Evidence for the formation of true inclusion complexes between the host 4 and C-60/C-70 was obtained from NMR spectroscopy performed at low temperatures. The experimental findings were fully corroborated by density functional theory (DFT) models performed on the host-guest assemblies (C-60@4 and C-70@4).pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationBARATA, Patrícia D.; [et al] – Fluorescent bis-calix[4]arene-carbazole conjugates: synthesis and inclusion complexation studies with fullerenes C-60 and C-70. Molecules. eISSN 1420-3049. Vol. 26, N.º 16 (2021), pp. 1-19pt_PT
dc.identifier.doi10.3390/molecules26165000pt_PT
dc.identifier.eissn1420-3049
dc.identifier.urihttp://hdl.handle.net/10400.21/13745
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.relationUIDB/00616/2021 - FCT/MCTESpt_PT
dc.relationUIDP/00616/2021 - FCT/MCTESpt_PT
dc.relation.publisherversionhttps://www.mdpi.com/1420-3049/26/16/5000pt_PT
dc.subjectCalix[4]arenept_PT
dc.subjectCarbazolept_PT
dc.subjectFluorescencept_PT
dc.subjectFullerenept_PT
dc.subjectSupramolecularpt_PT
dc.subjectHost-guest chemistrypt_PT
dc.titleFluorescent bis-calix[4]arene-carbazole conjugates: synthesis and inclusion complexation studies with fullerenes C-60 and C-70pt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage19pt_PT
oaire.citation.issue16pt_PT
oaire.citation.startPage1pt_PT
oaire.citation.titleMoleculespt_PT
oaire.citation.volume26pt_PT
person.familyNameBarata
person.familyNameCosta
person.familyNameCosta
person.familyNamePrata
person.givenNamePatrícia
person.givenNameAlexandra
person.givenNameSérgio
person.givenNameJosé Virgílio
person.identifier1090399
person.identifier191765
person.identifier.ciencia-idC019-9F30-0F99
person.identifier.ciencia-id4212-F7BF-D971
person.identifier.ciencia-idC11A-9130-8981
person.identifier.orcid0000-0001-8274-633X
person.identifier.orcid0000-0002-5518-6506
person.identifier.orcid0000-0003-2750-8325
person.identifier.orcid0000-0002-9068-2847
person.identifier.ridB-7214-2008
person.identifier.scopus-author-id8968446000
person.identifier.scopus-author-id8968446100
person.identifier.scopus-author-id9276778400
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication4ab8a01f-c11d-4b3b-b0cf-b21e5b634170
relation.isAuthorOfPublication5f3891cc-260d-41d3-b803-4fd17e3734bd
relation.isAuthorOfPublication7ad24bd6-c2f5-4fdc-b535-0ab9782063d7
relation.isAuthorOfPublication15e229f3-a619-4931-87eb-799091dc1601
relation.isAuthorOfPublication.latestForDiscovery4ab8a01f-c11d-4b3b-b0cf-b21e5b634170

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