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Calixarene/azolium cyclophane hybrids: synthesis, structure and conformations

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Abstract

The synthesis, structure, and conformational behaviour of three imidazolium cyclophanes that incorporate one or two 4-tert-butylphenol or 4-tert-butylanisole groups as meta-disubstituted linkers in the macrocycle is described. The cyclophanes containing anisole moieties adopt a cone conformation in the solid state, which, in solution, is not labile on the NMR timescale. The cyclophanes containing one or two phenol moieties adopt conformations other than the cone in the solid state and are labile in solution on the NMR timescale. The phenol cyclophanes are readily deprotonated, and structural and conformational studies for a variety of the associated cyclophanes are also reported.

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Acknowledgments

We thank the Australian Research Council for financial support (to M.V.B., A.H.W.) and an Australian Postgraduate Award (to V.J.H.), and Curtin University of Technology for a Research and Teaching Fellowship (to D.H.B.). We acknowledge the Centre of Microscopy, Characterisation and Analysis, The University of Western Australia (a facility funded by The University of Western Australia, the Australian Government and the State Government of Western Australia) for providing access to facilities, and for scientific and technical assistance.

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Authors and Affiliations

  1. School of Chemistry and Biochemistry M310, The University of Western Australia, Crawley, WA, 6009, Australia

    Valerie J. Hesler, Allan H. White, David H. Brown & Murray V. Baker

  2. School of Chemistry and Biochemistry and the Centre for Microscopy, Characterisation, and Analysis M310, The University of Western Australia, Crawley, WA, 6009, Australia

    Brian W. Skelton

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  1. Valerie J. Hesler
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Correspondence to Murray V. Baker.

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Dedicated to Jack Harrowfield and Jacques Vicens, two great chemists who have treated us to lots of interesting chemistry and interesting ways to think about it.

Electronic supplementary material

Below is the link to the electronic supplementary material.

10847_2015_491_MOESM1_ESM.pdf

Supplementary material 1 (PDF 149 kb). A table of selected bond distances and angles is supplied as electronic supplementary material. CCDC 1038207-1038210 contain the relevant cif files, which can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.ac.uk/data_request/cif.

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Hesler, V.J., Skelton, B.W., White, A.H. et al. Calixarene/azolium cyclophane hybrids: synthesis, structure and conformations. J Incl Phenom Macrocycl Chem 82, 53–69 (2015). https://doi.org/10.1007/s10847-015-0491-1

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  • DOI: https://doi.org/10.1007/s10847-015-0491-1

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