Quinoidal oligothiophenes with (acyl)cyanomethylene termini: Synthesis, characterization, properties, and solution processed n-channel organic field-effect transistors

Yuki Suzuki, Masafumi Shimawaki, Eigo Miyazaki, Itaru Osaka, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

A new class of oligothienoquinoidal derivatives with newly employed (acyl)cyanomethylene termini are reported. For the synthesis of (acyl)cyanomethylene-substituted thienoquinoidals, similar methods successfully employed for the synthesis of related dicyanomethylene-or ((alkyloxy)carbonyl) cyanomethylene-substituted thienoquinoidals were not applicable, and thus a new synthetic route was developed. The introduced (acyl)cyanomethylene terminal groups act both as a solublizing group to facilitate solution processability and an electron-withdrawing group to keep the LUMO energy levels sufficiently low for n-channel organic semiconductors. The LUMO energy levels estimated from their reduction potential are ∼4.2 eV below the vacuum level, which just falls in between those for the corresponding dicyanomethylene-and ((alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidals. This qualitatively agrees with the electron-withdrawing nature of the terminal groups; the order of the electron withdrawing nature is cyano-> acyl-> (alkyloxy)carbonyl-groups. Spin-coating chloroform solutions of (acyl)cyanomethylene-substituted thienoquinoidals gave homogeneous thin films on the Si/SiO2 substrates, and the thin films based on the terthienoquinoidal derivatives became highly crystalline upon thermal annealing. The annealed film acted as the active semiconducting channel in the FET devices under ambient conditions, and the electron mobilities extracted from the saturation regime were ∼0.06 cm2 V-1 s-1. These n-channel FET characteristics are nearly the same or slightly better than those of the FETs based on the related ((alkyloxy)carbonyl)cyanomethylene- terminated terthienoquinoidal, indicating that the (acyl)cyanomethylene moiety is a useful terminal group on the thienoquinoidals for the development of soluble n-channel organic semiconductors.

Original languageEnglish
Pages (from-to)795-804
Number of pages10
JournalChemistry of Materials
Volume23
Issue number3
DOIs
Publication statusPublished - 2011 Feb 8
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)
  • Materials Chemistry

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