Thiacalix(4)arene derivatives as radium ionophores: a study on the requirements for Ra2+ extraction

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Leeuwen, Fijs W.B. van and Beijleveld, Hans and Velders, Aldrik H. and Huskens, Jurriaan and Verboom, Willem and Reinhoudt, David N. (2005) Thiacalix(4)arene derivatives as radium ionophores: a study on the requirements for Ra2+ extraction. Organic and Biomolecular Chemistry, 3 (10). pp. 1993-2001. ISSN 1477-0520

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Abstract:The synthesis and NOE-based structural characterization is described of thiacalix[4]arene tricarboxylic acid ( 7), thiacalix[4]crown-5 and -6 monocarboxylic acids ( 2 and 5), and the bis(N-methylsulfonyl)thiacalix[4]crowns-5 and -6 ( 4a,b). The 226Ra2+ selectivity coefficients, log(KRaex/KMex), of the new thiacalix[4]arene derivatives are compared directly with those of thiacalix[4]crown-5 and -6 ( 1a,b), thiacalix[4]crown-5 and -6 dicarboxylic acids ( 3a,b), and thiacalix[4]arene di- and tetracarboxylic acids ( 6 and 8). Thiacalix[4]arene dicarboxylic acid ( 6) already exhibits a high 226Ra2+ selectivity, but this is significantly improved in the case of 3b, having an additional crown-(6-)ether bridge. The covalent combination of a crown ether and carboxylic acid substituents as in the thiacalix[4]arenes 2, 3a,b, 4a,b, and 5 gives a better 226Ra2+ selectivity in the presence of Sr2+ or Ba2+ than mixtures of dibenzo-21-crown-7 and thiacalix[4]arene dicarboxylic acid ( 6) or of pentadecanoic acid and thiacalix[4]crown-6 ( 1b).
Item Type:Article
Copyright:© Royal Society of Chemistry 2005
Faculty:
Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/52999
Official URL:http://dx.doi.org/10.1039/b501587a
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