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Poly(2-thiophene-3-yl-malonic acid), a Polythiophene with Two Carboxylic Acids Per Repeating Unit
dc.contributor.author | Bertran Cànovas, Òscar |
dc.contributor.author | Armelín Diggroc, Elaine Aparecida |
dc.contributor.author | Estrany Coda, Francesc |
dc.contributor.author | Gomes, Alex |
dc.contributor.author | Torras Costa, Juan |
dc.contributor.author | Alemán Llansó, Carlos |
dc.contributor.other | Universitat Politècnica de Catalunya. Departament d'Enginyeria Química |
dc.contributor.other | Universitat Politècnica de Catalunya. Departament de Física Aplicada |
dc.date.accessioned | 2010-05-31T09:29:40Z |
dc.date.available | 2010-05-31T09:29:40Z |
dc.date.created | 2010-04-22 |
dc.date.issued | 2010-04-22 |
dc.identifier.citation | Bertran, O. [et al.]. Poly(2-thiophene-3-yl-malonic acid), a Polythiophene with Two Carboxylic Acids Per Repeating Unit. "Journal of physical chemistry B", 22 Abril 2010, vol. 114, p. 6281-6290. |
dc.identifier.issn | 1520-6106 |
dc.identifier.uri | http://hdl.handle.net/2117/7429 |
dc.description.abstract | A new substituted polythiophene derivative bearing malonic acid, poly(2-thiophen-3-yl-malonic acid), has been prepared and characterized using a strategy that combines both experimental and theoretical methodologies. The chemical structure of this material has been investigated using FTIR and 1H NMR, and its molecular conformation has been determined using quantum mechanical calculations. Interestingly, the arrangement of the inter-ring dihedral angles was found to depend on the ionization degree of the material, that is, on the pH, which has been found completely soluble in aqueous base solution. Thus, the preferred anti-gauche conformation changes to syn-gauche when the negatively charged carboxylate groups transforms into neutral carboxylic acid. UV−vis experiments and quantum mechanical calculations on model systems with a head-to-tail regiochemistry showed that the lowest π−π* transition energy is 2.25 and 2.39 eV for the negatively charged and the neutral polymer, respectively. These values are slightly larger than those previously reported for other polythiophenes with bulky polar side groups. The polymer presents a good thermal stability with a decomposition temperature above 215 °C and an electrical conductivity of 10−5 S/cm, which is characteristic of semiconductor materials. Scanning electron microscopy micrographs showed that, after doping, the surface of this material displays regular distribution pores with irregular sizes. This surface suggests that poly(2-thiophen-3-yl-malonic acid) is a candidate for potential applications such as selective membranes for electrodialysis, wastewater treatment, or ion-selective membranes for biomedical uses. |
dc.format.extent | 10 p. |
dc.language.iso | eng |
dc.subject | Àrees temàtiques de la UPC::Enginyeria química::Química física |
dc.subject.lcsh | Molecular structure |
dc.subject.lcsh | Conducting polymers |
dc.title | Poly(2-thiophene-3-yl-malonic acid), a Polythiophene with Two Carboxylic Acids Per Repeating Unit |
dc.type | Article |
dc.subject.lemac | Polímers |
dc.subject.lemac | Estructura molecular |
dc.contributor.group | Universitat Politècnica de Catalunya. POL - Polímers Industrials Avançats i Biopolímers Tecnològics |
dc.contributor.group | Universitat Politècnica de Catalunya. IMEM - Innovació, Modelització i Enginyeria en (BIO) Materials |
dc.identifier.doi | 10.1021/jp1006796 |
dc.relation.publisherversion | http://pubs.acs.org/doi/abs/10.1021%2Fjp1006796 |
dc.rights.access | Restricted access - publisher's policy |
local.identifier.drac | 2523802 |
dc.description.version | Postprint (published version) |
local.citation.author | Bertran, O.; Armelin, E.A.; Estrany, F.; Gomes, A.; Torras, J.; Alemán, C. |
local.citation.publicationName | Journal of physical chemistry B |
local.citation.volume | 114 |
local.citation.startingPage | 6281 |
local.citation.endingPage | 6290 |
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