Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene Derivatives: Synthesis and effect of sulfur positions on their transistor properties

Shuhei Nishinaga, Masato Mitani, Hiroki Mori, Toshihiro Okamoto, Jun Takeya, Yasushi Nishihara

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    Bis[1]benzothieno[5,4-d:5¤,4¤-d¤]benzo[1,2-b:4,5-b¤]dithiophene (BBTBDT-2) and its phenyl-substituted derivative were successfully synthesized and characterized. From DFT calculations, highest occupied molecular orbitals (HOMOs) of both compounds are well delocalized and large orbital coefficients exist on sulfur atoms. Single-crystal X-ray analysis revealed that BBTBDT-2 derivatives formed herringbone structures in the solid state. In particular, BBTBDT-2 formed a layer-by-layer structure with effective 2D charge-carrier transporting capability. The fabricated OFETs based on BBTBDT-2 gave mobility up to 0.49 cm2 V11 s11 in the vacuum-deposited thin films, which is the highest value among BBTBDT derivatives including our previously reported syn-counterparts. We have also clarified a detailed structureproperty relationship of sulfur positions and phenyl substituents as indicated by theoretical calculation, GIWAXS, and AFM analyses.

    Original languageEnglish
    Pages (from-to)1107-1116
    Number of pages10
    JournalBulletin of the Chemical Society of Japan
    Volume92
    Issue number6
    DOIs
    Publication statusPublished - 2019

    Keywords

    • Organic field-effect transistor
    • Polycyclic aromatic compounds
    • Structural isomers of thienoacene

    ASJC Scopus subject areas

    • Chemistry(all)

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