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Issue 5, 2011
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Squaramides: physical properties, synthesis and applications

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Abstract

Squaramides are remarkable four-membered ring systems derived from squaric acid that are able to form up to four hydrogen bonds. A high affinity for hydrogen bonding is driven through a concomitant increase in aromaticity of the ring. This hydrogen bonding and aromatic switching, in combination with structural rigidity, have been exploited in many of the applications of squaramides. Substituted squaramides can be accessed via modular synthesis under relatively mild or aqueous conditions, making them ideal units for bioconjugation and supramolecular chemistry. In this tutorial review the fundamental electronic and structural properties of squaramides are explored to rationalise the geometry, conformation, reactivity and biological activity.

Graphical abstract: Squaramides: physical properties, synthesis and applications

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Article information


Submitted
01 Dec 2010
First published
14 Mar 2011

Chem. Soc. Rev., 2011,40, 2330-2346
Article type
Tutorial Review

Squaramides: physical properties, synthesis and applications

R. Ian Storer, C. Aciro and L. H. Jones, Chem. Soc. Rev., 2011, 40, 2330
DOI: 10.1039/C0CS00200C

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