Alkyl Chain Orientations in Dicyanomethylene-Substituted 2,5-Di(thiophen-2-yl)thieno-[3,2-b]thienoquinoid: Impact on Solid-State and Thin-Film Transistor Performance

Authors

  • Qinghe Wu,

    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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  • Shendong Ren,

    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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  • Mao Wang,

    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
    2. School of Materials Science and Engineering, East China University of Science and Technology, Shanghai, 200237, China
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  • Xiaolan Qiao,

    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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  • Hongxiang Li,

    Corresponding author
    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
    • Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

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  • Xike Gao,

    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
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  • Xiaodi Yang,

    1. Laboratory of Advanced Materials, Fudan University, Shanghai, 200438, China
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  • Daoben Zhu

    Corresponding author
    1. Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China
    2. Beijing National Laboratory for Molecular Sciences, Key Laboratory of Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China
    • Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.

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Abstract

A series of dicyanomethylene-substituted 2,5-di(thiophen-2-yl)thieno[3,2-b]thieno-quinoids, in which soluble alkyl chains (2-decyltetradecyls) are substituted at different positions (namely, 2,2′-positions (Compound 1); 3,3′- positions (Compound 2); 6,6′-positions (Compound 3)), are strategically designed and successfully synthesized. The photophysical and electrochemical properties as well as molecular packing of these new compounds are thoroughly investigated. Thin film transistor measurements reveal that Compounds 1–3 display markedly different charge transport performance. The solution processed thin film transistors of Compound 2 exhibits the highest electron mobility of up to 0.22 cm2 V−1 s−1 under ambient conditions, one and three orders of magnitude higher than those of Compounds 3 and 1, respectively, demonstrating the strong impact of alkyl chain orientations on transistor performance.

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