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C 4 Dissymmetric resorcinarene derivatives: synthesis, crystal structure and micelle formation

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Abstract

The synthesis of a C 4 dissymmetric resorcinarene tetracarboxylic acid derivative and determination of its critical micelle concentration is reported. The tetrahydroxy derivative was prepared by reduction of the tetra-acid. The low-temperature single crystal X-ray structure of the methyl ester derivative of the tetra-acid is also reported. This crystallised with two independent molecules of similar boat (flattened cone) conformation within the asymmetric unit.

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Scheme 1
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Fig. 2
Scheme 2

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Notes

  1. Calixarene nomenclature follows that recommended by IUPAC. See: Favre et al. [27] and McIldowie et al. [5] for calixarene examples.

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Authors and Affiliations

  1. Department of Chemistry and Nanochemistry Research Institute, Curtin University, Bentley, WA, 6845, Australia

    Matthew J. McIldowie, Mauro Mocerino & Mark I. Ogden

  2. School of Chemistry and Biochemistry and Centre for Microscopy, Characterisation and Analysis, M313, The University of Western Australia, Crawley, WA, 6009, Australia

    Brian W. Skelton

  3. School of Chemistry and Biochemistry, M313, The University of Western Australia, Crawley, WA, 6009, Australia

    Allan H. White

Authors
  1. Matthew J. McIldowie
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  2. Mauro Mocerino
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  3. Mark I. Ogden
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  4. Brian W. Skelton
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  5. Allan H. White
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Correspondence to Mauro Mocerino.

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Dedicated to Professor Jack Harrowfield on the occasion of his 70th birthday.

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McIldowie, M.J., Mocerino, M., Ogden, M.I. et al. C 4 Dissymmetric resorcinarene derivatives: synthesis, crystal structure and micelle formation. J Incl Phenom Macrocycl Chem 82, 47–51 (2015). https://doi.org/10.1007/s10847-015-0525-8

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  • DOI: https://doi.org/10.1007/s10847-015-0525-8

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