Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes
dc.contributor.author | Fei, Zhuping | |
dc.contributor.author | Boufflet, Pierre | |
dc.contributor.author | Wood, Sebastian | |
dc.contributor.author | Wade, Jessica | |
dc.contributor.author | Moriarty, John | |
dc.contributor.author | Gann, Eliot | |
dc.contributor.author | Ratcliff, Erin L. | |
dc.contributor.author | McNeill, Christopher R. | |
dc.contributor.author | Sirringhaus, Henning | |
dc.contributor.author | Kim, Ji-Seon | |
dc.contributor.author | Heeney, Martin | |
dc.date.accessioned | 2016-02-25T13:33:17Z | |
dc.date.available | 2016-02-25T13:33:17Z | |
dc.date.issued | 2015-05-21 | |
dc.identifier.citation | Fei 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.issn | 0002-7863 | |
dc.identifier.issn | 1520-5126 | |
dc.identifier.pmid | 25994804 | |
dc.identifier.doi | 10.1021/jacs.5b02785 | |
dc.identifier.uri | http://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.sponsorship | This 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.publisher | American Chemical Society (ACS) | |
dc.title | Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes | |
dc.type | Article | |
dc.identifier.journal | Journal of the American Chemical Society | |
dc.contributor.institution | Imperial College London, London, United Kingdom | |
dc.contributor.institution | University of Cambridge, Cambridge, United Kingdom | |
dc.contributor.institution | Monash University, Melbourne, Australia | |
dc.contributor.institution | Australian Synchrotron, Clayton, Australia | |
dc.contributor.institution | University of Arizona, Tucson, United States | |
kaust.grant.number | CRG-1-2012-THO-015 | |
dc.date.published-online | 2015-05-21 | |
dc.date.published-print | 2015-06-03 |