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Highly Emissive and Electrochemically Stable Thienylene Vinylene Oligomers and Copolymers: An Unusual Effect of Alkylsulfanyl Substituents

Authors

  • Shehzad Jeeva,

    1. Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada)
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  • Olena Lukoyanova,

    1. Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada)
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  • Athan Karas,

    1. Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada)
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  • Afshin Dadvand,

    1. Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada)
    2. Centre Énergie, Matériaux et Télécommunications Institut National de la Recherche Scientifique Varennes Quebec J3X 1S2 (Canada)
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  • Federico Rosei,

    1. Centre Énergie, Matériaux et Télécommunications Institut National de la Recherche Scientifique Varennes Quebec J3X 1S2 (Canada)
    2. Centre for Self-Assembled Chemical Structures McGill University Montreal, Quebec, H3A 2K6 (Canada)
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  • Dmitrii F. Perepichka

    Corresponding author
    1. Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada)
    2. Centre for Self-Assembled Chemical Structures McGill University Montreal, Quebec, H3A 2K6 (Canada)
    • Department of Chemistry McGill University Montreal, Quebec, H3A 2K6 (Canada).
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Abstract

The synthesis, unexpected efficient photoluminescence, and reversible electrochemical p- and n-doping of new conjugated thienylene vinylene materials functionalized with alkylsulfanyl substituents poly(trithienylene vinylene) (PTTV) and poly(dithienylvinyl-co-benzothiadiazole) (PDTVB) along with dithienylvinylene-based oligomers is reported. The materials are studied by thermal and X-ray diffraction analysis, optical spectroscopy, cyclic voltammetry, and spectroelectrochemistry. Organic field-effect transistors (OFETs) are fabricated with PTTV and PDTVB. The polymers, prepared by Stille polycondensation, exhibit good thermal stability and a photoluminescent quantum yield in the range 34%–68%. Low bandgaps (1.5–1.8 eV), estimated by optical and electrochemical measurements along with high stability of both redox states, suggest that these structures are promising materials for photovoltaic applications. OFETs fabricated with PDTVB reveal a hole mobility of 7 × 10−3 cm2 V−1 s−1 with on/off ratio 105, which are comparatively high values for completely amorphous polymer semiconductors.

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