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Synthesis and Cation-Binding Properties of Novel p-Isopropenylcalix[n]arenes and Their Acetylated Derivatives

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Abstract

A novel two-step method was developed to prepare individual p-isopropenylcalix[n]arenes [n=4, 6, 8]. In the first step, linear phenolic oligomers were prepared in a basic medium from p-isopropenylphenol and paraformaldehyde. The second step, cyclization of the linear oligomers was carried out at higher temperatures. Ethylene glycol was used as medium, and sodium tetraborate-decahydrate as the catalyst. O-Acetylated derivatives were obtained by acetylation of the phenolic hydroxyl groups of p-isopropenylcalix[n]arenes [n=4, 6, 8]. The p-isopropenyl-calix[n]arenes and their acetylated derivatives were characterized by IR, 1H NMR and UV spectroscopy, and elemental analysis. Their ability to extract metal cations from aqueous solutions was evaluated via metal picrate extraction experiments. A parallel investigation of the cation-binding ability of the p-tert-butylcalix[n]arenes [n=4, 6, 8] and their acetylated derivatives was also performed. The p-isopropenylcalix[6]arene hexaacetate is the most effective extracting agent for metal picrates, and shows strong affinity towards Rb cation.

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Acknowledgements

The authors are indebted to the financial support from University of Chemical Technology and Metallurgy, Sofia, Bulgaria (Grant No 10143).

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Authors and Affiliations

  1. Department of Polymer Engineering, University of Chemical Technology and Metallurgy, Kliment Ohridski 8, 1756, Sofia, Bulgaria

    S. Yordanova, S. Miloshev & B. Diakovski

  2. Institute of Polymers, Bulgarian Academy of Sciences, 1113, Sofia, Bulgaria

    I. Berlinova

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  1. S. Yordanova
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  2. S. Miloshev
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  3. I. Berlinova
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  4. B. Diakovski
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Correspondence to S. Miloshev.

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Yordanova, S., Miloshev, S., Berlinova, I. et al. Synthesis and Cation-Binding Properties of Novel p-Isopropenylcalix[n]arenes and Their Acetylated Derivatives . J Incl Phenom Macrocycl Chem 56, 337–344 (2006). https://doi.org/10.1007/s10847-006-9104-3

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  • DOI: https://doi.org/10.1007/s10847-006-9104-3

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