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Related Experiment Videos

Octaphenylbiphenylene and dodecaphenyltriptycene.

Jun Lu1, Jiajia Zhang, Xianfeng Shen

  • 1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, USA.

Journal of the American Chemical Society
|July 4, 2002
PubMed
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Researchers synthesized octaphenylbiphenylene and two novel tetraphenylbenzyne dimers, including a highly crowded dodecaphenyltriptycene. X-ray crystallography revealed unique structures, with dodecaphenyltriptycene forming a channel structure with benzene solvates.

Area of Science:

  • Organic Chemistry
  • Materials Science
  • Crystallography

Background:

  • Tetraphenylbenzyne is a strained alkyne with unique reactivity.
  • Synthesis of highly substituted polycyclic aromatic hydrocarbons (PAHs) presents significant challenges.
  • Understanding the structural diversity of benzyne dimers is crucial for exploring new chemical space.

Purpose of the Study:

  • To synthesize and characterize novel dimers of tetraphenylbenzyne.
  • To investigate the structural properties of highly crowded polycyclic aromatic hydrocarbons.
  • To explore the formation of inclusion compounds with novel PAH structures.

Main Methods:

  • Diazotization of 3,4,5,6-tetraphenylanthranilic acid to form octaphenylbiphenylene.
  • Synthesis of 1,2,3,4,5,6,7,8-octaphenylanthracene from commercial precursors.

Related Experiment Videos

  • Reaction of tetraphenylbenzyne with octaphenylanthracene to yield dodecaphenyltriptycene.
  • X-ray crystallography for structural determination of synthesized compounds and solvates.

    • Main Results:

    • Octaphenylbiphenylene, an expected dimer of tetraphenylbenzyne, was synthesized in low yield.
    • An abnormal dimer, 1,2,3,8,9,10-hexaphenyldibenzo[fg,op]naphthacene, a saddle-shaped PAH, was identified and structurally characterized.
    • The most crowded triptycene derivative, 1,2,3,4,5,6,7,8,13,14,15,16-dodecaphenyltriptycene, was synthesized.
    • The X-ray structure of dodecaphenyltriptycene nonabenzene solvate revealed a channel-containing structure with over 50% benzene in the unit cell.

    Conclusions:

    • The synthesis of tetraphenylbenzyne dimers demonstrates diverse reaction pathways.
    • The structural characterization of novel PAHs expands knowledge of molecular architecture.
    • The formation of inclusion compounds highlights the potential for host-guest chemistry with complex organic frameworks.