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'Twisted' isophthalamide analogues.

Simon J Brooks1, Louise S Evans, Philip A Gale

  • 1School of Chemistry, University of Southampton, Southampton, SO17 1BJ, UK.

Chemical Communications (Cambridge, England)
|February 3, 2005
PubMed
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Steric interactions in 1,3-dicarboxamidoanthraquinones twist anion binding sites. A crystal structure reveals a fluoride complex acting as a hydrogen-bonding corner in a molecular box.

Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Crystal Engineering

Background:

  • 1,3-dicarboxamidoanthraquinones are known for their ability to form specific binding sites.
  • Steric interactions can be used to control the geometry of these binding sites.
  • Anion recognition is a key area in supramolecular chemistry.

Purpose of the Study:

  • To investigate the use of steric interactions in 1,3-dicarboxamidoanthraquinones to create twisted isophthalamide-like anion binding sites.
  • To determine the crystal structure of a fluoride complex with a bis-3,5-dichlorophenylamide derivative.
  • To understand the role of the receptor in forming a fluoride-containing molecular box.

Main Methods:

  • Synthesis of a bis-3,5-dichlorophenylamide derivative of 1,3-dicarboxamidoanthraquinone.

Related Experiment Videos

  • Complexation with fluoride ions.
  • X-ray crystallography to determine the solid-state structure.

    • Main Results:

    • Steric interactions successfully twisted the isophthalamide-like anion binding sites.
    • The crystal structure revealed a '2 + 2' molecular box containing fluoride ions.
    • The receptor molecule acted as a 'hydrogen-bonding corner' within this box.

    Conclusions:

    • 1,3-dicarboxamidoanthraquinones are effective scaffolds for creating sterically controlled anion binding sites.
    • The 'hydrogen-bonding corner' motif is crucial for the self-assembly of fluoride-containing molecular boxes.
    • This work advances the design of receptors for anion recognition and supramolecular assembly.