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Giant cyclophanes built from polyphenyl aromatic substructures

Pascal1, Barnett, Qiao

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

The Journal of Organic Chemistry
|November 14, 2000
PubMed
Summary
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Two large macrocyclic compounds called cyclophanes were synthesized. One cyclophane has a collapsed structure, while the other features large cavities forming channels for solvents.

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Crystal Engineering

Background:

  • Cyclophanes are macrocyclic organic compounds known for their unique structural properties.
  • The synthesis of large cyclophanes often requires complex multi-step procedures.
  • Controlling the conformation and solid-state packing of macrocycles is crucial for their applications.

Purpose of the Study:

  • To develop efficient synthetic routes for very large cyclophanes.
  • To investigate the structural characteristics and solid-state behavior of novel cyclophane architectures.
  • To explore the potential of these macrocycles in host-guest chemistry and materials science.

Main Methods:

  • Short synthetic pathways (approx. 5 steps) using commercially available starting materials.

Related Experiment Videos

  • Preparation of two distinct large cyclophanes utilizing octaphenylnaphthalene or 1,3-bis(pentaphenylphenyl)benzene subunits.
  • X-ray crystallographic analysis to determine molecular conformation and crystal packing.

    • Main Results:

    • Successful synthesis of two large cyclophanes (C(132)H(92)O(8)S(4) and C(172)H(120)O(8)S(4)) in a concise manner.
    • X-ray analysis revealed a 'collapsed' conformation for one cyclophane (3).
    • The second cyclophane (4) exhibited significant central cavities, forming solvent-accessible channels in the crystal.

    Conclusions:

    • Efficient synthetic strategies enable the preparation of complex, large-scale cyclophanes.
    • The structural diversity of cyclophanes can be tuned, leading to different conformational preferences.
    • The formation of solvent channels in cyclophane 4 suggests potential for applications in molecular recognition and separation.