Thiophene-diazine molecular semiconductors: Synthesis, structural, electrochemical, optical, and electronic structural properties; Implementation in organic field-effect transistors

Rocío Ponce Ortiz, Juan Casado, Víctor Hernández, Juan T.López Navarrete, Joseph A. Letizia, Mark A. Ratner, Antonio Facchetti, Tobin J. Marks

Research output: Contribution to journalArticle

69 Citations (Scopus)

Abstract

The synthesis, structural, electrochemical, optical, and electronic structure properties of a new azinethiophene semiconductor family are reported and compared to those of analogous oligothiophenes. The new molecules are: 5,5′-bis(6-(thien-2-yl)pyrimid-4-yl)-2,2′-dithiophene (1), 5,5′-bis(6-(5-hexylthien-2-yl)pyrimid-4-yl)-2,2′-dithiophene (3), and 5,5′-bis(6-(thien-2-yl)pyridazin-3-yl))-2,2′-dithiophene (2). Electrochemical experiments demonstrate that introduction of electron-poor heteroaromatic rings into the oligothiophene core significantly enhances electron affinity. Thin-film transistors were fabricated with these materials and evaluated both in vacuum and in air. We find that although diazine substitution is important in tuning oligothiophene orbital energetics, these oligomers are p-channel semiconductors and the field-effect transistor (FET) charge transport properties are remarkably similar to these of unsubstituted oligothiophenes. The combined computational-experimental analysis of the molecular and thin film properties indicates that these diazine-containing oligothiophenes essentially behave as π-extended bithiophenes. Interestingly, despite strong intermolecular interactions, high solid-state fluorescence efficiencies are observed for these new derivatives. Such emission characteristics suggest that these materials behave as more extended π systems, which should be advantageous in light-emitting transistors.

Original languageEnglish
Pages (from-to)5023-5039
Number of pages17
JournalChemistry - A European Journal
Volume15
Issue number20
DOIs
Publication statusPublished - May 11 2009

Keywords

  • Density functional calculations
  • Electrochemistry
  • P-type mobility
  • Semiconductors transistors

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry

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