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Thiadiazolo-Azaacenes.

Matthias Müller1, Silke Koser1, Olena Tverskoy1

  • 1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 28, 2019
PubMed
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Researchers synthesized novel fused organic molecules with multiple fused rings. These compounds, featuring thiadiazole units, show stability but limited electron affinity due to their structure.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Azaacenes are a class of organic compounds with potential applications in electronics.
  • Thiadiazole units can modify the electronic properties of organic molecules.
  • Controlling the electronic properties of extended pi-conjugated systems is crucial for materials development.

Purpose of the Study:

  • To synthesize and characterize novel bis- and tetrakis(thiadiazolo)-appended di- and tetraazaacenes.
  • To investigate the structural and electronic properties of these extended pi-conjugated systems.
  • To explore the relationship between molecular structure and electron affinity.

Main Methods:

  • Condensation reactions between benzo-bis(thiadiazole)-4,5-dione and aromatic di- and tetraamines.
Keywords:
X-ray crystallographybuilding blockscondensationheteroacenesthiadiazole

Related Experiment Videos

  • Characterization of the synthesized compounds using spectroscopic and analytical techniques.
  • Evaluation of the electronic properties, including electron affinity.

    • Main Results:

    • Successful synthesis of azaacene derivatives with up to seven catenated rings, appended with thiadiazole units.
    • The synthesized compounds exhibit stability but can be insoluble.
    • Soluble derivatives are processible but do not display enhanced electron affinities.
    • The electronic properties are influenced by the resonance separation between the thiadiazole units and the acene core.

    Conclusions:

    • The study presents a new class of extended pi-conjugated molecules with potential for further research.
    • The structural design effectively maximizes Clar-sextets, influencing electronic properties.
    • Further modifications may be needed to enhance electron affinities for specific applications.