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dc.contributor.authorArmelín Diggroc, Elaine Aparecida
dc.contributor.authorBertran Cànovas, Òscar
dc.contributor.authorEstrany Coda, Francesc
dc.contributor.authorSalvatella, Roser
dc.contributor.authorAlemán Llansó, Carlos
dc.contributor.otherEscola Universitària d'Enginyeria Tècnica Industrial de Barcelona
dc.contributor.otherUniversitat Politècnica de Catalunya. Departament d'Enginyeria Química
dc.date.accessioned2010-04-14T10:45:35Z
dc.date.available2010-04-14T10:45:35Z
dc.date.created2009-05-27
dc.date.issued2009-05-27
dc.identifier.citationArmelin, E.A. [et al.]. Characterization and properties of a polythiophene with a malonic acid dimethyl ester side group. "European polymer journal", 27 Maig 2009, vol. 45, p. 2211-2221.
dc.identifier.issn0014-3057
dc.identifier.urihttp://hdl.handle.net/2117/6930
dc.description.abstractA new polythiophene derivative bearing a malonic acid dimethyl ester substituent attached to the 3-position of the repeat unit has been prepared by chemical oxidative-coupling polymerization. The chemical structure of poly(2-thiophen-3-yl-malonic acid dimethyl ester) has been analyzed by FTIR and 1H NMR spectroscopy and, additionally, the distribution of the head-to-tail and head-to-head diads arising from polymerization was found to be a 75–25%. The glass transition temperature identified for this polymer was 17.6 °C lower than that recently determined for a closely related polythiophene derivative, in which the ester substituent arose from acrylic acid rather than from malonic acid. On the other hand, the electrical conductivity of the new material, which was soluble in polar solvents but not in water, was higher than that typically found for poly(3-alkylthiophene) derivatives. Ab initio quantum mechanical calculations on simple model compounds were used to predict the regiochemistry of the polymer chain, which was in excellent agreement with the experimental observation, and the conformational preferences of both the inter-ring dihedral angle and the bulky side group. Interestingly, calculations predict that the inter-ring dihedral angles adopt a syn-gauche conformation rather than the anti-gauche arrangement typically found in substituted polythiophenes. Thus, in this case the former conformation reduces the strong repulsive interactions induced by the bulky substituent. The lowest π–π* transition energy derived from calculations on an idealized molecular model is in agreement with the experimental estimation determined using UV–vis spectroscopy. This electronic property is significantly higher for poly(2-thiophen-3-yl-malonic acid dimethyl ester) than for other substituted polythiophene derivatives, which is consequence of the geometrical distortions induced by bulky side group.
dc.format.extent11 p.
dc.language.isoeng
dc.rightsAttribution-NonCommercial-NoDerivs 3.0 Spain
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/es/
dc.subjectÀrees temàtiques de la UPC::Enginyeria química
dc.titleCharacterization and properties of a polythiophene with a malonic acid dimethyl ester side group
dc.typeArticle
dc.subject.lemacÀcids
dc.subject.lemacPolímers conductors
dc.contributor.groupUniversitat Politècnica de Catalunya. POL - Polímers Industrials Avançats i Biopolímers Tecnològics
dc.contributor.groupUniversitat Politècnica de Catalunya. IMEM - Innovació, Modelització i Enginyeria en (BIO) Materials
dc.identifier.doi10.1016/j.eurpolymj.2009.05.024
dc.description.peerreviewedPeer Reviewed
dc.rights.accessRestricted access - publisher's policy
drac.iddocument2194701
dc.description.versionPostprint (updated version)
upcommons.citation.authorArmelin, E.A.; Bertran, O.; Estrany, F.; Salvatella, R.; Alemán, C.
upcommons.citation.publishedtrue
upcommons.citation.publicationNameEuropean polymer journal
upcommons.citation.volume45
upcommons.citation.startingPage2211
upcommons.citation.endingPage2221


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