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Versatile α,ω-Disubstituted Tetrathienoacene Semiconductors for High Performance Organic Thin-Film Transistors

Authors

  • Jangdae Youn,

    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
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  • Peng-Yi Huang,

    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
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  • Yu-Wen Huang,

    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
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  • Ming-Chou Chen,

    Corresponding author
    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
    • Ming-Chou Chen, Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan.

      Antonio Facchetti, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

      Tobin J. Marks, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

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  • Yu-Jou Lin,

    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
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  • Hui Huang,

    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
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  • Rocio Ponce Ortiz,

    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
    2. Department of Physical Chemistry, University of Malaga, 29071, Malaga, Spain
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  • Charlotte Stern,

    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
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  • Ming-Che Chung,

    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
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  • Chieh-Yuan Feng,

    1. Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan
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  • Liang-Hsiang Chen,

    1. Process Technology Division, Display Technology Center, Industrial Technology Research Institute, Chung Hsing Rd., Chutung, Hsinchu, Taiwan 31040, R.O.C.
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  • Antonio Facchetti,

    Corresponding author
    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
    • Ming-Chou Chen, Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan.

      Antonio Facchetti, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

      Tobin J. Marks, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

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  • Tobin J. Marks

    Corresponding author
    1. Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA
    • Ming-Chou Chen, Department of Chemistry, National Central University, Jhong-Li 32054, Taiwan.

      Antonio Facchetti, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

      Tobin J. Marks, Department of Chemistry and the Materials Research Center, Northwestern University, 2145 Sheridan Rd., Evanston, IL 60208-3113, USA

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Abstract

Facile one-pot [1 + 1 + 2] and [2 + 1 + 1] syntheses of thieno[3,2-b]thieno[2′,3′:4,5]thieno[2,3-d]thiophene (tetrathienoacene; TTA) semiconductors are described which enable the efficient realization of a new TTA-based series for organic thin-film transistors (OTFTs). For the perfluorophenyl end-functionalized derivative DFP-TTA, the molecular structure is determined by single-crystal X-ray diffraction. This material exhibits n-channel transport with a mobility as high as 0.30 cm2V−1s−1 and a high on-off ratio of 1.8 × 107. Thus, DFP-TTA has one of the highest electron mobilities of any fused thiophene semiconductor yet discovered. For the phenyl-substituted analogue, DP-TTA, p-channel transport is observed with a mobility as high as 0.21 cm2V−1s−1. For the 2-benzothiazolyl (BS-) containing derivative, DBS-TTA, p-channel transport is still exhibited with a hole mobility close to 2 × 10−3 cm2V−1s−1. Within this family, carrier mobility magnitudes are strongly dependent on the semiconductor growth conditions and the gate dielectric surface treatment.

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