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Developing 9,10-anthracene Derivatives: Optical, Electrochemical, Thermal, and Electrical Characterization.

Mikhail Y Vorona1, Nathan J Yutronkie2, Owen A Melville1

  • 1Department of Chemical and Biological Engineering, University of Ottawa, 161 Louis Pasteur, Ottawa K1N 6N5, ON, Canada.

Materials (Basel, Switzerland)
|August 29, 2019
PubMed
Summary

Synthesizing novel anthracene molecules functionalized at the 9,10-positions offers a way to tune thermal stability without impacting optical properties. This research explores their use in organic thin-film transistors (OTFTs).

Keywords:
OTFTsSuzuki-Miyaura cross-coupling reactionanthracenecrystalpackingsemiconductorthin filmtransistor

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Area of Science:

  • Materials Science
  • Organic Electronics
  • Supramolecular Chemistry

Background:

  • Anthracene-based semiconductors are noted for air stability, planarity, and suitable energy levels.
  • Their potential in organic electronics necessitates understanding structure-property relationships.

Purpose of the Study:

  • To synthesize and characterize novel 9,10-anthracene derivatives.
  • To investigate the impact of phenyl functionalization on optical, electrochemical, thermal, and solid-state properties.
  • To evaluate their performance in preliminary organic thin-film transistors (OTFTs).

Main Methods:

  • Synthesis of seven novel 9,10-anthracene-based molecules.
  • Characterization of optical, electrochemical, and thermal properties.
  • Single crystal X-ray diffraction for structural analysis.
  • Fabrication and testing of organic thin-film transistors (OTFTs).

Main Results:

  • Functionalization at the 9,10-positions showed minimal changes in optical properties (±0.10 eV).
  • Phenyl derivative choice significantly influenced thermal stability (decomposition temperature > 258 °C).
  • Solid-state arrangement remained largely unaffected by the phenyl substituents.
  • Preliminary OTFTs demonstrated the potential of these materials.

Conclusions:

  • Functionalization at the 9,10-position of anthracene is an effective strategy for tuning thermal stability.
  • Optical properties and solid-state arrangement are minimally affected by this functionalization.
  • These anthracene derivatives show promise for applications in organic electronics, particularly OTFTs.