Low Bandgap Bistetracene-Based Organic Semiconductors Exhibiting Air Stability, High Aromaticity and Mobility

Kamal Sbargoud, Masashi Mamada, Tanguy Jousselin-Oba, Yasunori Takeda, Shizuo Tokito, Abderrahim Yassar, Jérôme Marrot, Michel Frigoli

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    The benchmark of soluble organic semiconductors based on acenes is the 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS–PEN). However TIPS–PEN still suffers from photoinduced oxidation due to its low degree of aromaticity. Increasing the aromaticity while keeping similar optical and electrochemical properties as well as a shape suitable for good hole transport can be achieved with two-dimensional polycyclic aromatic hydrocarbons (2D-PAHs). Herein, we present an efficient synthesis and characterization of bistetracene derivatives that exhibit a band gap up to 1.71 eV and an increased stability up to 21 times compared to TIPS–PEN and mobility over 0.1 cm2 V−1 s−1 in solution-processed organic field-effect transistors. Based on simple structural consideration, the high stability is attributed to the aromaticity of the bistetracene which is comparable to an anthrancene along each tetracene. According to Clar's sextet rule, the bistetracene should be best regarded as two anthracenes fused at the face bridged by two ethylenic spacers. The synthesis path paves the way towards the preparation of ambipolar and/or longer 2D-PAHs such as bispentacenes and could give rise to organic semiconductors with interesting properties.

    Original languageEnglish
    Pages (from-to)5076-5080
    Number of pages5
    JournalChemistry - A European Journal
    Volume23
    Issue number21
    DOIs
    Publication statusPublished - 2017

    All Science Journal Classification (ASJC) codes

    • Catalysis
    • Organic Chemistry

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