Dialkoxybithiazole: A new building block for head-to-head polymer semiconductors

Xugang Guo, Jordan Quinn, Zhihua Chen, Hakan Usta, Yan Zheng, Yu Xia, Jonathan W. Hennek, Rocío Ponce Ortiz, Tobin J. Marks, Antonio Facchetti

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130 Citations (Scopus)

Abstract

Polymer semiconductors have received great attention for organic electronics due to the low fabrication cost offered by solution-based printing techniques. To enable the desired solubility/processability and carrier mobility, polymers are functionalized with hydrocarbon chains by strategically manipulating the alkylation patterns. Note that head-to-head (HH) linkages have traditionally been avoided because the induced backbone torsion leads to poor π-π overlap and amorphous film microstructures, and hence to low carrier mobilities. We report here the synthesis of a new building block for HH linkages, 4,4′-dialkoxy-5,5′-bithiazole (BTzOR), and its incorporation into polymers for high performance organic thin-film transistors. The small oxygen van der Waals radius and intramolecular S(thiazolyl) ⋯O(alkoxy) attraction promote HH macromolecular architectures with extensive π-conjugation, low bandgaps (1.40-1.63 eV), and high crystallinity. In comparison to previously reported 3,3′-dialkoxy-2,2′-bithiophene (BTOR), BTzOR is a promising building block in view of thiazole geometric and electronic properties: (a) replacing (thiophene)C-H with (thiazole)N reduces steric encumbrance in -BTzOR-Ar.06-0.25 cm2/(V s)) in organic thin-film transistors, as well as enhanced Ion:Ioff ratios and greater ambient stability than the BTOR analogues. These geometric and electronic properties make BTzOR a promising building block for new classes of polymer semiconductors, and the synthetic route to BTzOR reported here should be adaptable to many other bithiazole-based building blocks.

Original languageEnglish
Pages (from-to)1986-1996
Number of pages11
JournalJournal of the American Chemical Society
Volume135
Issue number5
DOIs
Publication statusPublished - Feb 6 2013

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Guo, X., Quinn, J., Chen, Z., Usta, H., Zheng, Y., Xia, Y., Hennek, J. W., Ortiz, R. P., Marks, T. J., & Facchetti, A. (2013). Dialkoxybithiazole: A new building block for head-to-head polymer semiconductors. Journal of the American Chemical Society, 135(5), 1986-1996. https://doi.org/10.1021/ja3120532