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    Influence of Backbone Fluorination in Regioregular Poly(3-alkyl-4-fluoro)thiophenes

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    Type
    Article
    Authors
    Fei, Zhuping
    Boufflet, Pierre
    Wood, Sebastian
    Wade, Jessica
    Moriarty, John
    Gann, Eliot
    Ratcliff, Erin L.
    McNeill, Christopher R.
    Sirringhaus, Henning
    Kim, Ji-Seon
    Heeney, Martin
    KAUST Grant Number
    CRG-1-2012-THO-015
    Date
    2015-05-21
    Online Publication Date
    2015-05-21
    Print Publication Date
    2015-06-03
    Permanent link to this record
    http://hdl.handle.net/10754/598621
    
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    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.
    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.
    Sponsors
    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.
    Publisher
    American Chemical Society (ACS)
    Journal
    Journal of the American Chemical Society
    DOI
    10.1021/jacs.5b02785
    PubMed ID
    25994804
    ae974a485f413a2113503eed53cd6c53
    10.1021/jacs.5b02785
    Scopus Count
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