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A solid-state fluorescence sensor for nitroaromatics and nitroanilines based on a conjugated Calix[4]arene polymer

2020-01Journal article Restricted access
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dc.contributor.authorPrata, José V.
dc.contributor.authorCosta, Alexandra I.
dc.contributor.authorTeixeira, Carlos
dc.date.accessioned2020-06-05T12:43:01Z
dc.date.available2020-06-05T12:43:01Z
dc.date.issued2020-01
dc.description.abstractA new conjugated polymer possessing calix[4]arene-oxacyclophane units wired-in-series by phenyleneethynylene linkers was synthesized by a Sonogashira-Hagihara cross-coupling method in high yield. The polymer was structurally characterized by FTIR and 1H/13C/HSQC NMR techniques, and its average Mn (38.5 kDa) retrieved from GPC analysis. The polymer is highly emissive (ΦF =0.55) and exhibits a longer-than-usual excited-state lifetime (1.80 ns) for a phenyleneethynylene type polymer. Similar photo physical properties (absorption and fluorescence emission) were observed in solution and insolid-state. This stems from the presence of bulky calixarene moieties along the polymer chains which prevent interchain staking and the formation of ground-state aggregates and/or non-emissive exciplexes, both deleterious to solid-state materials envisioned for fluorescence sensing applications. Moreover, the intrinsic molecular recognition capabilities of its two rigid inner cavities (calixarene and cyclophane sub-units), allied with the high three-dimensionality of the macromolecule that creates additional interstitial voids around the molecular receptors, can boost its sensory responses towards specific analytes. A high sensitive response was observed in the detection of nitroaromatics and nitroanilines in neat vapour phases by casted films of the polymer. The largest sensitivitieswereobtainedfor2,4-dinitrotoluene (a taggant for the explosive TNT;>85% of fluorescence quenching upon 1 min exposure) and ortho-nitroaniline (90% of emission reduction in 30s).The sensory responses attained in solid-state are discussed on the basis of the electron affinities of the analytes and their electrostatic interactions with polymer films.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationPRATA, José V.; COSTA, Alexandra I.; TEIXEIRA, Carlos M. – A solid-state fluorescence sensor for nitroaromatics and nitroanilines based on a conjugated Calix[4]arene polymer. Journal of Fluorescence. ISSN 1053-0509. Vol. 30, N.º 1 (2020), pp. 41-50pt_PT
dc.identifier.doihttps://doi.org/10.1007/s10895-019-02466-1pt_PT
dc.identifier.issn1053-0509
dc.identifier.issn1573-4994
dc.identifier.urihttp://hdl.handle.net/10400.21/11779
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherSpringerpt_PT
dc.relationUID/QUI/00616/2019 - FCT/ MCTESpt_PT
dc.relation.publisherversionhttps://link.springer.com/content/pdf/10.1007/s10895-019-02466-1.pdfpt_PT
dc.subjectFluorescencept_PT
dc.subjectCalix[4]arenept_PT
dc.subjectOxacyclophanept_PT
dc.subjectPolymerpt_PT
dc.subjectNitroanilinespt_PT
dc.subjectNitroaromaticspt_PT
dc.subjectSensorpt_PT
dc.subjectExplosivespt_PT
dc.titleA solid-state fluorescence sensor for nitroaromatics and nitroanilines based on a conjugated Calix[4]arene polymerpt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage50pt_PT
oaire.citation.issue1pt_PT
oaire.citation.startPage41pt_PT
oaire.citation.titleJournal of Fluorescencept_PT
oaire.citation.volume30pt_PT
person.familyNamePrata
person.familyNameCosta
person.familyNameTeixeira
person.givenNameJosé Virgílio
person.givenNameAlexandra
person.givenNameCarlos
person.identifier191765
person.identifier.ciencia-idC11A-9130-8981
person.identifier.ciencia-id4212-F7BF-D971
person.identifier.ciencia-id5611-E882-68CE
person.identifier.orcid0000-0002-9068-2847
person.identifier.orcid0000-0002-5518-6506
person.identifier.orcid0000-0002-7303-3570
person.identifier.ridB-7214-2008
person.identifier.scopus-author-id9276778400
person.identifier.scopus-author-id8968446100
rcaap.rightsclosedAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication15e229f3-a619-4931-87eb-799091dc1601
relation.isAuthorOfPublication5f3891cc-260d-41d3-b803-4fd17e3734bd
relation.isAuthorOfPublication0efbcdd2-32af-4543-9169-0a67238d8b0e
relation.isAuthorOfPublication.latestForDiscovery5f3891cc-260d-41d3-b803-4fd17e3734bd

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