Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes.
We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylhexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation of a single regioisomer...
| Publicado en: | Journal of the American Chemical Society Vol. 137; no. 21; pp. 6866 - 6880 |
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| Autores principales: | , , , , , , , , , , |
| Formato: | Artículo |
| Publicado: |
American Chemical Society
6/3/2015
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=hlh&AN=103347993&site=ehost-live header: @attributes: shortDbName: hlh uiTerm: 103347993 longDbName: Humanities International Complete uiTag: AN controlInfo: bkinfo: jinfo: jid: 00027863 ACS jtl: Journal of the American Chemical Society issn: 00027863 maglogo: N pubinfo: dt: 6/3/2015 vid: 137 iid: 21 pid: 997 pub: American Chemical Society artinfo: ui: 103347993 10.1021/jacs.5b02785 ppf: 6866 ppct: 14 formats: tig: atl: Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes. aug: au: Zhuping Fei Boufflet, Pierre Wood, Sebastian Wade, Jessica Moriarty, John Gann, Eliot Ratcliff, Erin L. McNeill, Christopher R. Sirringhaus, Henning Ji-Seon Kim Heeney, Martin affil: Department of Chemistry and Centre for Plastic Electronics, Imperial College London, Exhibition Rd, London SW7 2AZ, U.K Department of Physics and Centre for Plastic Electronics, Imperial College London, Exhibition Rd, London SW7 2AZ, U.K Cavendish Laboratory, University of Cambridge, J J Thomson Avenue, Cambridge CB3 OHE, U.K. Department of Materials Science and Engineering, Monash University, Clayton, Victoria 3800, Australia Australian Synchrotron, 800 Blackburn Road, Clayton, Victoria 3168, Australia Department of Materials Science and Engineering, University of Arizona, Tucson, Arizona 85721, United States su: Fluorination Polythiophenes Density functional theory Alkyl compounds Polymerization Fluorine sug: subj: Fluorination Polythiophenes Density functional theory Alkyl compounds Polymerization Fluorine ab: We report two strategies toward the synthesis of 3-alkyl-4-fluorothiophenes containing straight (hexyl and octyl) and branched (2-ethylhexyl) alkyl groups. We demonstrate that treatment of the dibrominated monomer with 1 equiv of alkyl Grignard reagent leads to the formation of a single regioisomer as a result of the pronounced directing effect of the fluorine group. Polymerization of the resulting species affords highly regioregular poly(3-alkyl-4-fluoro)- thiophenes. Comparison of their properties to those of the analogous non-fluorinated polymers shows that backbone fluorination leads to an increase in the polymer ionization potential without a significant change in optical band gap. Fluorination also results in an enhanced tendency to aggregate in solution, which is ascribed to a more co-planar backbone on the basis of Raman and DFT calculations. Average charge carrier mobilities in field-effect transistors are found to increase by up to a factor of 5 for the fluorinated polymers. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y dt: @attributes: year: 2015 holdings: @attributes: islocal: N |
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