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Engineering Nanorafts of Calixarene Polyphosphonates

  1. Thomas E. Clark1,
  2. Mohamed Makha Dr.1,
  3. Alexandre N. Sobolev Dr.1,
  4. Henry Rohrs Dr.2,
  5. Jerry L. Atwood Prof.3,
  6. Colin L. Raston Prof.1

Article first published online: 11 MAR 2008

DOI: 10.1002/chem.200701472

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 14, Issue 13, pages 3931–3938, April 28, 2008

Additional Information

How to Cite

Clark, T., Makha, M., Sobolev, A., Rohrs, H., Atwood, J. and Raston, C. (2008), Engineering Nanorafts of Calixarene Polyphosphonates. Chemistry - A European Journal, 14: 3931–3938. doi: 10.1002/chem.200701472

Author Information

  1. 1

    Department of Chemistry, The University of Western Australia, Crawley, WA 6009, Australia, Fax: (+61) 08-6488-1005

  2. 2

    Department of Chemistry, University of Washington, St. Louis, MO 63130, USA

  3. 3

    Department of Chemistry, University of Missouri-Columbia, Columbia, MO 65211, USA

Publication History

  1. Issue published online: 18 APR 2008
  2. Article first published online: 11 MAR 2008
  3. Manuscript Received: 17 SEP 2007

Funded by

  • ARC
  • NSF
  • NIH. Grant Number: P41RR00954
  • The University of Western Australia

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Keywords:

  • calixarenes;
  • nanostructures;
  • process intensification;
  • self-assembly;
  • supramolecular chemistry

Graphical Abstract

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Tunable self-assembly of calixarenes: A water-soluble calix[4]arene bearing p-substituted phosphonic acid groups is synthesized in five steps. The hydrogen bonding of the acidic groups dominates the self-assembly processes, which include formation of 3.0(3) nm and 20(2) nm nanorafts in water (see figure) and in the gas phase.

Abstract

The water-soluble calix[4]arene bearing p-substituted phosphonic acid groups is accessible in five steps in overall 62 % yield, with the hydrogen-bonding prowess of the acidic groups dominating its self-assembly processes. These include the formation of 3.0(3) nm and 20(2) nm nanorafts of the calixarene in water using spinning disc processing, stabilized by acetonitrile, and nanorafts in the gas phase (≤20 molecules). The 20(2) nm particles transform into 3.0(3) nm particles prior to crystallization into a compact bilayer, whereas crystallization in the presence of large organic molecules gives an expanded bilayer interposed by layers of water molecules.

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