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Hexapole [9]Helicene.

Yonggen Wang1, Zhibo Yin1, Yanpeng Zhu1

  • 1School of Chemistry, Sun Yat-Sen University, Guangzhou, 510275, China.

Angewandte Chemie (International Ed. in English)
|November 21, 2018
PubMed
Summary

Researchers synthesized the first hexapole [9]helicene (H9H) through a novel cyclotrimerization and dehydrocyclization pathway. This new molecule exhibits unique structural distortions and interesting optical and electronic properties.

Keywords:
chiralityhelicenenonplanarsteric hindrance

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Helicenes are polycyclic aromatic hydrocarbons with a helical structure, presenting unique stereochemical and photophysical properties.
  • The synthesis of larger helicenes, particularly beyond the [6]helicene level, remains a significant challenge in organic chemistry.
  • Previous methods for synthesizing [9]helicenes are complex and often yield limited quantities.

Purpose of the Study:

  • To report the first synthesis of a hexapole [9]helicene (H9H).
  • To investigate the structural, optical, and electronic properties of this novel H9H molecule.
  • To explore a new synthetic strategy for constructing complex, highly distorted polycyclic aromatic systems.

Main Methods:

  • Co-catalyzed [2+2+2] cyclotrimerization of a dinaphthopyrene (DNP) functionalized alkyne to form a hexaaryl benzene precursor.
  • Dehydrocyclization of the precursor to yield the target hexapole [9]helicene (H9H).
  • Single-crystal X-ray diffraction analysis, chiral resolution, and characterization of optical and electronic properties.

Main Results:

  • Successful synthesis of the first hexapole [9]helicene (H9H) via a multi-step sequence.
  • X-ray crystallography revealed highly distorted and sterically hindered structural features of both the precursor and H9H.
  • Characterization provided insights into the chiral, optical, and electronic behavior of the newly synthesized H9H.

Conclusions:

  • The developed synthetic route provides access to a novel class of highly complex helicene architectures.
  • The unique structural features of H9H are confirmed and contribute to its distinct properties.
  • This work expands the scope of accessible helicene structures and their potential applications.