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Squaramides: physical properties, synthesis and applications.

R Ian Storer1, Caroline Aciro, Lyn H Jones

  • 1Worldwide Medicinal Chemistry, Pfizer Global Research and Development, Ramsgate Road, Sandwich, Kent, CT13 9NJ, UK. ian.storer@pfizer.com

Chemical Society Reviews
|March 15, 2011
PubMed
Summary

Squaramides, derived from squaric acid, are versatile four-membered rings that form strong hydrogen bonds. Their unique properties enable applications in bioconjugation and supramolecular chemistry.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Squaramides are four-membered cyclic compounds derived from squaric acid.
  • They exhibit a remarkable capacity for forming up to four hydrogen bonds.
  • This strong hydrogen bonding is linked to an increase in the aromaticity of the ring system.

Purpose of the Study:

  • To explore the fundamental electronic and structural properties of squaramides.
  • To rationalize the geometry, conformation, reactivity, and biological activity of squaramides.
  • To highlight the potential of squaramides in bioconjugation and supramolecular chemistry.

Main Methods:

  • Review of fundamental electronic and structural properties.
  • Analysis of hydrogen bonding capabilities and aromaticity.
  • Discussion of synthetic accessibility and applications.

Main Results:

  • Squaramides possess unique hydrogen bonding and aromatic switching capabilities.
  • Structural rigidity contributes to their versatile applications.
  • Modular synthesis allows for mild or aqueous conditions, ideal for bioconjugation.

Conclusions:

  • Squaramides are highly adaptable building blocks in chemistry.
  • Their properties make them valuable for advanced applications.
  • Further exploration of squaramides will drive innovation in supramolecular and medicinal chemistry.