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 journalArticle

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 - Jan 1 2019

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Sulfur
Transistors
Derivatives
Organic field effect transistors
X ray analysis
Molecular orbitals
Charge carriers
Discrete Fourier transforms
Single crystals
Vacuum
Thin films
Atoms

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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

In: Bulletin of the Chemical Society of Japan, Vol. 92, No. 6, 01.01.2019, p. 1107-1116.

Research output: Contribution to journalArticle

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