Synthesis, characterization, and transistor response of tetrathia-[7]-helicene precursors and derivatives

Choongik Kim, Tobin J. Marks, Antonio Facchetti, Michele Schiavo, Alberto Bossi, Stefano Maiorana, Emanuela Licandro, Francesco Todescato, Stefano Toffanin, Michele Muccini, Claudia Graiff, Antonio Tiripicchio

Research output: Contribution to journalArticle

38 Citations (Scopus)

Abstract

In this paper we report polycyclic, fully-conjugated, heteroaromatic compounds 1-5, two of them having a helical shape (tetrathia-[7]-helicenes 1 and 2), and explore their potential use as p-type semiconductors for organic thin-film transistors (OTFTs). Furthermore, we describe their optical absorption, emission, and electrochemical properties. In addition, the single crystal X-ray diffraction structure for compound 3 is reported. Thin films of all compounds were fabricated on several substrates at different temperatures by physical vapor deposition, and were characterized by optical spectroscopy, wide-angle X-ray diffraction, atomic force microscopy, and TFT measurements. The AFM images of compound 1 exhibit an interesting tubular morphology for films deposited at room temperature. This is the first observation of a compound with a helical shape leading to a nanowire-like morphology. In agreement with the molecular structure/morphology, only compound 4 is a p-type semiconductor with good carrier mobility.

Original languageEnglish
Pages (from-to)1511-1520
Number of pages10
JournalOrganic Electronics
Volume10
Issue number8
DOIs
Publication statusPublished - Dec 2009

    Fingerprint

Keywords

  • Organic thin-film transistor
  • Vacuum deposition
  • p-Type semiconductor

ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Biomaterials
  • Chemistry(all)
  • Condensed Matter Physics
  • Materials Chemistry
  • Electrical and Electronic Engineering

Cite this

Kim, C., Marks, T. J., Facchetti, A., Schiavo, M., Bossi, A., Maiorana, S., Licandro, E., Todescato, F., Toffanin, S., Muccini, M., Graiff, C., & Tiripicchio, A. (2009). Synthesis, characterization, and transistor response of tetrathia-[7]-helicene precursors and derivatives. Organic Electronics, 10(8), 1511-1520. https://doi.org/10.1016/j.orgel.2009.08.018