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dc.contributor.authorFei, Zhuping
dc.contributor.authorBoufflet, Pierre
dc.contributor.authorWood, Sebastian
dc.contributor.authorWade, Jessica
dc.contributor.authorMoriarty, John
dc.contributor.authorGann, Eliot
dc.contributor.authorRatcliff, Erin L.
dc.contributor.authorMcNeill, Christopher R.
dc.contributor.authorSirringhaus, Henning
dc.contributor.authorKim, Ji-Seon
dc.contributor.authorHeeney, Martin
dc.date.accessioned2016-02-25T13:33:17Z
dc.date.available2016-02-25T13:33:17Z
dc.date.issued2015-05-21
dc.identifier.citationFei Z, Boufflet P, Wood S, Wade J, Moriarty J, et al. (2015) Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes. Journal of the American Chemical Society 137: 6866–6879. Available: http://dx.doi.org/10.1021/jacs.5b02785.
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126
dc.identifier.pmid25994804
dc.identifier.doi10.1021/jacs.5b02785
dc.identifier.urihttp://hdl.handle.net/10754/598621
dc.description.abstract© 2015 American Chemical Society. 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.
dc.description.sponsorshipThis work was supported by EPSRC grants EP/G060738/1 and EP/K029843/1, a KAUST Competitive Research grant under agreement no. CRG-1-2012-THO-015, and the Australian Research Council (FT100100275, DP130102616). We thank Dr. Scott E. Watkins (CSIRO Melbourne) for the PESA measurements. Part of this research was undertaken on the SAXS/WAXS beamline at the Australian Synchrotron, Victoria, Australia.
dc.publisherAmerican Chemical Society (ACS)
dc.titleInfluence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes
dc.typeArticle
dc.identifier.journalJournal of the American Chemical Society
dc.contributor.institutionImperial College London, London, United Kingdom
dc.contributor.institutionUniversity of Cambridge, Cambridge, United Kingdom
dc.contributor.institutionMonash University, Melbourne, Australia
dc.contributor.institutionAustralian Synchrotron, Clayton, Australia
dc.contributor.institutionUniversity of Arizona, Tucson, United States
kaust.grant.numberCRG-1-2012-THO-015
dc.date.published-online2015-05-21
dc.date.published-print2015-06-03


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