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Synthesis, structure, and optical properties of an alternating calix[4]arene-based meta-linked phenylene ethynylene copolymer

2010-11-15Journal article Open access
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dc.contributor.authorD. Barata, Patrícia
dc.contributor.authorCosta, Alexandra
dc.contributor.authorFerreira, Luis F. V.
dc.contributor.authorPrata, José Virgílio
dc.date.accessioned2011-11-24T12:38:58Z
dc.date.available2011-11-24T12:38:58Z
dc.date.issued2010-11-15
dc.description.abstractNovel alternating copolymers comprising biscalix[4]arene-p-phenylene ethynylene and m-phenylene ethynylene units (CALIX-m-PPE) were synthesized using the Sonogashira-Hagihara cross-coupling polymerization. Good isolated yields (60-80%) were achieved for the polymers that show M-n ranging from 1.4 x 10(4) to 5.1 x 10(4) gmol(-1) (gel permeation chromatography analysis), depending on specific polymerization conditions. The structural analysis of CALIX-m-PPE was performed by H-1, C-13, C-13-H-1 heteronuclear single quantum correlation (HSQC), C-13-H-1 heteronuclear multiple bond correlation (HMBC), correlation spectroscopy (COSY), and nuclear overhauser effect spectroscopy (NOESY) in addition to Fourier transform-Infrared spectroscopy and microanalysis allowing its full characterization. Depending on the reaction setup, variable amounts (16-45%) of diyne units were found in polymers although their photophysical properties are essentially the same. It is demonstrated that CALIX-m-PPE does not form ground-or excited-state interchain interactions owing to the highly crowded environment of the main-chain imparted by both calix[4]arene side units which behave as insulators inhibiting main-chain pi-pi staking. It was also found that the luminescent properties of CALIX-m-PPE are markedly different from those of an all-p-linked phenylene ethynylene copolymer (CALIX-p-PPE) previously reported. The unexpected appearance of a low-energy emission band at 426 nm, in addition to the locally excited-state emission (365 nm), together with a quite low fluorescence quantum yield (Phi = 0.02) and a double-exponential decay dynamics led to the formulation of an intramolecular exciplex as the new emissive species.por
dc.identifier.citationBarata P, Costa A, Ferreira L, Prata J.Synthesis, Structure, and Optical Properties of an Alternating Calix[4]arene-Based Meta-Linked Phenylene Ethynylene Copolymer. Journal of Polymer Science Part A-Polymer Chemistry. 2010; 48 (22): 5040-5052.por
dc.identifier.issn0887-624X
dc.identifier.urihttp://hdl.handle.net/10400.21/531
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherJohn Wiley & Sons INCpor
dc.relation.ispartofseries22
dc.subjectCalixarenepor
dc.subjectFluorescencepor
dc.subjectIntramolecular exciplexpor
dc.subjectMeta-linkedpor
dc.subjectPhenylene ethynylene polymerpor
dc.titleSynthesis, structure, and optical properties of an alternating calix[4]arene-based meta-linked phenylene ethynylene copolymerpor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.conferencePlaceHobokenpor
oaire.citation.endPage5052por
oaire.citation.issue48por
oaire.citation.startPage5040por
oaire.citation.titleJournal of Polymer Science Part A-Polymer Chemistrypor
person.familyNameBarata
person.familyNameCosta
person.familyNamePrata
person.givenNamePatrícia
person.givenNameAlexandra
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.orcid0000-0002-9068-2847
person.identifier.ridB-7214-2008
person.identifier.scopus-author-id8968446000
person.identifier.scopus-author-id8968446100
person.identifier.scopus-author-id9276778400
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication4ab8a01f-c11d-4b3b-b0cf-b21e5b634170
relation.isAuthorOfPublication5f3891cc-260d-41d3-b803-4fd17e3734bd
relation.isAuthorOfPublication15e229f3-a619-4931-87eb-799091dc1601
relation.isAuthorOfPublication.latestForDiscovery4ab8a01f-c11d-4b3b-b0cf-b21e5b634170

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