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Liquid–liquid extraction studies with 4,4′-biphenylene-spaced bis-β-diketones

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Abstract

4,4′-biphenylene spaced lipophilic bis-β-diketone ligands of the type 4,4′-bis(RC(O)CH2C(O))C12H8 (R = Pr, Ph, hexyl, octyl, nonyl) have been prepared and used for the liquid–liquid extraction of d-block metal ions. These ligands are expected to interact with divalent metal ions to form charge-neutral trinuclear metallocycles of type [M3(L 3)3(solvent)] as has been demonstrated with the previously reported derivative of H2 L 3 (R = tBu), the X-ray structure of which is reported. Liquid–liquid extraction studies were performed in a two-phase water/chloroform system employing a radiotracer technique for cobalt(II) and zinc(II). These experiments involved the systematic variation of ligand, metal and 4-ethylpyridine concentrations to probe the stoichiometries of the species extracted. Synergistic extraction was observed when 4-ethylpyridine was present with the ligand in the organic phase. Competitive extraction studies demonstrated the ligands are highly selective for copper(II) over cobalt(II), nickel(II), zinc(II) and cadmium(II).

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Acknowledgements

We thank the Australian Research Council, the Deutsche Forschungsgemeinschaft, the International Program Development Fund (University of Sydney) and the Marie Curie IIF scheme of the 7th EU Framework Program for support. We thank Prof. Peter Tasker and Dr. Ross Gordon from the University of Edinburgh for helpful discussions. We thank Prof. Len Lindoy for his assistance and advice throughout the project.

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  1. Department of Chemistry, The University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, UK

    Jack K. Clegg

  2. School of Chemistry, The University of Sydney, Sydney, NSW, 2006, Australia

    Jack K. Clegg, David J. Bray & Katrina A. Jolliffe

  3. Department of Chemistry and Food Chemistry, Technical University Dresden, 01062, Dresden, Germany

    Bianca Antonioli, Karsten Gloe, Kerstin Gloe, Olga N. Kataeva & Marco Wenzel

  4. A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan, 420088, Russia

    Olga N. Kataeva

  5. School of Pharmacy and Molecular Sciences, James Cook University, Townsville, 4814, Australia

    George V. Meehan

  6. School of Chemistry, The University of Southampton, Southampton, SO17 1BJ, UK

    Marco Wenzel

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  1. Jack K. Clegg
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  2. Bianca Antonioli
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  3. David J. Bray
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  4. Karsten Gloe
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  5. Kerstin Gloe
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  6. Katrina A. Jolliffe
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  7. Olga N. Kataeva
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  8. George V. Meehan
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  9. Marco Wenzel
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Correspondence to Jack K. Clegg.

Additional information

Dedicated to Mrs Fay Lindoy on the occasion of Len’s 75th birthday.

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Clegg, J.K., Antonioli, B., Bray, D.J. et al. Liquid–liquid extraction studies with 4,4′-biphenylene-spaced bis-β-diketones. J Incl Phenom Macrocycl Chem 71, 319–329 (2011). https://doi.org/10.1007/s10847-011-9954-1

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  • DOI: https://doi.org/10.1007/s10847-011-9954-1

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