((Alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidal compounds: A New class of soluble n-channel organic semiconductors for air-stable organic field-effect transistors

Yuki Suzuki, Eigo Miyazaki, Kazuo Takimiya

Research output: Contribution to journalArticlepeer-review

102 Citations (Scopus)

Abstract

A new n-channel semiconductor class for organic field-effect transistors (OFETs) based on thienoquinoidal structures is reported. A newly employed terminal group, the ((alkyloxy)carbonyl)cyanomethylene moiety, plays two important roles in the thienoquinoidal compounds: i.e., as an electron-withdrawing group to keep the LUMO energy level sufficiently low for acting as an n-channel organic semiconductor and as a solubilizing group to facilitate solution processability. For the construction of this class of compounds, a new, straightforward synthetic method was established and applied to oligothienoquinoidal and fused thienoquinoidal systems. When both core and alkyl groups in the ester moiety were tuned, the thienoquinoidals exhibited good solubility, stability in the atmosphere, and electron-accepting properties, as well as solution processability. Solution-processed FETs based on the terthienoquinoid derivative with ((n-alkyloxy)carbonyl)cyanomethylene moieties exhibit good electron mobilities (μ ∼0.015 cm2 V-1 s-1) and Ion/Ioff ≈ 105 under ambient conditions. Vapor-processed FETs using the benzodithienoquinoidal derivative showed similar n-channel FET characteristics.

Original languageEnglish
Pages (from-to)10453-10466
Number of pages14
JournalJournal of the American Chemical Society
Volume132
Issue number30
DOIs
Publication statusPublished - 2010 Aug 4
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of '((Alkyloxy)carbonyl)cyanomethylene-substituted thienoquinoidal compounds: A New class of soluble n-channel organic semiconductors for air-stable organic field-effect transistors'. Together they form a unique fingerprint.

Cite this