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Dodecaphenyltetracene.

Yonglong Xiao1, Joel T Mague1, Russell H Schmehl1

  • 1Department of Chemistry, Tulane University, New Orleans, LA, 70118, USA.

Angewandte Chemie (International Ed. in English)
|January 11, 2019
PubMed
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Dodecaphenyltetracene, the largest perphenylacene, was synthesized and characterized. This highly luminescent molecule exhibits a unique twisted structure and stable electrochemical properties.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Perphenylacenes are polycyclic aromatic hydrocarbons with potential applications in organic electronics.
  • Synthesizing larger perphenylacenes presents challenges due to steric hindrance and reactivity.
  • Controlling molecular geometry is crucial for tuning electronic and optical properties.

Purpose of the Study:

  • To synthesize and characterize dodecaphenyltetracene, the largest perphenylacene reported to date.
  • To investigate the structural, photophysical, and electrochemical properties of this novel compound.
  • To explore the impact of extensive phenyl substitution on acene stability and reactivity.

Main Methods:

  • Multi-step organic synthesis utilizing tetraphenylfuran, hexaphenylisobenzofuran, and a tetrabrominated diphenylbenzene precursor.
Keywords:
acenespolycyclic aromatic hydrocarbonspolyphenyl aromatic compounds

Related Experiment Videos

  • X-ray crystallography for detailed structural elucidation.
  • Photoluminescence spectroscopy to assess luminescence properties.
  • Electrochemical techniques (cyclic voltammetry) to determine oxidation and reduction potentials.

    • Main Results:

    • Successful synthesis of dodecaphenyltetracene in three steps.
    • X-ray structure revealed a D2-symmetric molecule with a significant 97° end-to-end twist.
    • The molecule is deep red and highly luminescent.
    • Peripheral phenyl groups effectively encapsulate the central acene core, leading to reduced reactivity.
    • Demonstrated reversible electrochemical oxidation and reduction, indicating electronic stability.

    Conclusions:

    • Dodecaphenyltetracene represents a significant advancement in the synthesis of large perphenylacenes.
    • The twisted, encapsulated structure imparts remarkable stability and unique photophysical properties.
    • This work provides insights into the design of robust organic materials with tunable electronic characteristics.