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Aminopyridyl derivative of thiacalix[4]arene-carboxylic acid as ionizable highly selective Ag+ ionophore

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Abstract

A novel mono-ionizable receptor 2 possessing three aminopyridyl and one carboxylic group in 1,3-alternate conformation based on thiacalix[4]arene, confirmed by single crystal X-ray analysis, was prepared. For competitive solvent extraction of alkali metal (Na+, K+ and Cs+) and some transition metal (Cu2+, Zn2+, TI+, Ag+) cations from aqueous solutions into chloroform, it was found that the introduction of proton-ionizable group (carboxylic acid moiety) into the aminopyridyl-thiacalix[4]arene derivative could further improve its Ag+ extractability with high selectivity.

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References

  1. Bozkurt, S., Karakucuk, A., Sirit, A., Yilmaz, M.: Synthesis of two calix[4]arene diamide derivatives for extraction of chromium (VI). Tetrahedron 61, 10443–10448 (2005)

    Article  CAS  Google Scholar 

  2. Fontàs, C., Antićo, E., Vocanson, F., Lamartine, R., Seta, P.: Efficient thiacalix[4]arenes for the extraction and separation of Au(III), Pd(II) and Pt(IV) metal ions from acidic media incorporated in membranes and solid phases. Sep. Purif. Technol. 54, 322–328 (2007)

    Article  Google Scholar 

  3. Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarenes 2001. Kluwer Academic Publishers, Dordrecht (2001)

    Google Scholar 

  4. Harrowfield, J., Vicens, J. (eds.): Calixarenes in the Nanoworld. Springer, Dordrecht, The Netherlands (2007)

    Google Scholar 

  5. Iki, N., Kabuto, C., Fukushima, T., Kumagai, H., Takeya, H., Miyanari, S., Miyashi, T., Miyano, S.: Synthesis of p-tert-butylthiacalix[4]arene and its inclusion properties. Tetrahedron 56, 1437–1443 (2000)

    Article  CAS  Google Scholar 

  6. Hosseini, M.W.: Thia-, mercapto-, and thiamercaptocalix[4]arenes. In: Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.) Calixarenes 2001, pp. 110–129. Kluwer Academic Publishers, Dordrecht, The Netherlands (2001)

    Google Scholar 

  7. Iki, N., Miyano, S.: Can thiacalixarenes surpass calixarenes? J. Incl. Phenom. Macro. Chem. 41, 99–105 (2001)

    Article  CAS  Google Scholar 

  8. Morohashi, N., Narumi, F., Iki, N., Hattori, N.T., Miyano, S.: Thiacalixarenes. Chem. Rev. 106, 5291–5316 (2006)

    Article  CAS  Google Scholar 

  9. Li, X., Gong, S.L., Yang, W.P., Chen, Y.Y.: An efficient Ag+ ionophore based on thiacalix[4]arene. Chin. J. Chem. 26, 709–715 (2008)

    Article  CAS  Google Scholar 

  10. Csokai, V., Grün, A., Balazs, B., Simon, A., Toth, G., Bitter, I.: Functionalized thiacalix- and calix[4]arene-based Ag+ ionophores: synthesis and comparative NMR study. Tetrahedron 62, 10215–10222 (2006)

    Article  CAS  Google Scholar 

  11. Bhalla, V., Babu, J.N., Kumar, M., Hattorib, T., Miyano, S.: Synthesis and binding studies of novel thiacalixpodands and bisthiacalixarenes having O, O″-dialkylated thiacalix[4]arene unit(s) of 1, 3-alternate conformation. Tetrahedron Lett. 48, 1581–1585 (2007)

    Article  CAS  Google Scholar 

  12. Evtugyn, G.A., Stoikov, I.I., Beljyakova, S.V., Shamagsumova, R.V., Stoikova, E.E., Zhukov, A.Yu., Antipin, I.S., Budnikov, H.C.: Ag selective electrode based on glassy carbon electrode covered with polyaniline and thiacalix[4]arene as neutral carrier. Talanta 71, 1720–1727 (2007)

    Article  CAS  Google Scholar 

  13. Tu, C.Q., Surowiec, K., Bartsch, R.A.: Novel calix[4]arene-thiacrown ether for selective and efficient extraction of Ba(II), Pb(II), and Hg(II). J. Incl. Phenom. Macro. Chem. 58, 361–366 (2009)

    Article  Google Scholar 

  14. Tu, C.Q., Surowiec, K., Gegay, J., Purkiss, D.W., Bartsch, R.A.: Di-ionizable calix[4]arene-1, 2-crown-5 and -crown-6 ethers in cone conformations: synthesis and divalent metal ion extraction. Tetrahedron 64, 1187–1196 (2008)

    Article  CAS  Google Scholar 

  15. Zhang, D.M., Cao, X.D., Purkiss, D.W., Bartsch, R.A.: Di-ionizable p-tert-butylcalix[4]arene-1, 2-crown-3 ligands in cone and 1, 2-alternate conformations: synthesis and metal ion extraction. Org. Biomol. Chem. 5, 1251–1259 (2007)

    Article  CAS  Google Scholar 

  16. Tu, C.Q., Surowiec, K., Bartsch, R.A.: Efficient divalent metal cation extractions with di-ionizable calix[4]arene-1, 2-crown-4 compounds. Tetrahedron 63, 4184–4189 (2007)

    Article  CAS  Google Scholar 

  17. Tu, C.Q., Surowiec, K., Gegay, J., Purkiss, D.W., Bartsch, R.A.: Di-ionizable p-tert-butylcalix[4]arene-1, 2-crown-5 and -crown-6 compounds in the cone conformation: synthesis and alkaline earth metal cation extraction. Org. Biomol. Chem. 4, 2938–2944 (2006)

    Article  CAS  Google Scholar 

  18. Tu, C.Q., Surowiec, K., Bartsch, R.A.: Di-ionizable p-tert-butylcalix[4]arene-1, 2-crown-4 ligands: synthesis and high divalent metal ion extraction selectivity. Tetrahedron Lett. 47, 3443–3446 (2006)

    Article  CAS  Google Scholar 

  19. van Leeuwen, F.W.B., Beijleveld, H., Miermans, C.J.H., Huskens, J., Verboom, W., Reinhoudt, D.N.: Ionizable (Thia)calix[4]crowns as highly selective 226Ra2+ ionophores. Anal. Chem. 77, 4611–4617 (2005)

    Article  Google Scholar 

  20. Li, X., Gong, S.L., Yang, W.P., Chen, Y.Y., Meng, X.G.: The influence of isomerism on the self-assembly behavior and complexation property of 1, 3-alternate tetraaminopyridyl-thiacalix[4]arene derivatives. Tetrahedron 64, 6230–6237 (2008)

    Article  CAS  Google Scholar 

  21. Kumagai, J., Hasegawa, M., Miyanari, S., Sugawa, Y., Sato, Y., Hori, T., Ueda, S., Kamiyama, H., Miyano, S.: Facile synthesis of p-tert-butylthiacalix[4]arene by reaction of p-tertbutylphenol with elemental sulphur in the presence of a base. Tetrahedron Lett. 38, 3971–3972 (1997)

    Article  CAS  Google Scholar 

  22. Akdas, H., Mislin, G., Graf, E., Hosseini, M.W., Cian, A.D., Fischer, J.: Synthesis and solid state structural analysis of conformers of Tetrakis((ethoxycarbonyl)methoxy)tetrathiacalix[4]arene. Tetrahedron Lett. 40, 2113–2116 (1999)

    Article  CAS  Google Scholar 

  23. Zlatušková, P., Stibor, I., Tkadlecová, M., Lhoták, P.: Novel anion receptors based on thiacalix[4]arene derivatives. Tetrahedron 60, 11383–11390 (2004)

    Article  Google Scholar 

  24. Akkus, G.U., Cebeci, C.: Synthesis and extraction studies of polymeric phthalimido functionalized calix[4]arene. J. Incl. Phenom. Macro. Chem. 62, 303–309 (2004)

    Article  Google Scholar 

  25. Sheldrick, G.M.: SHELXS97, A Program for Crystal Structure Solution. University of Göttingen, Göttingen, Germany (1997)

    Google Scholar 

  26. Sheldrick, G.M.: SHELXL97, A Program for Crystal Structure Refinement. University of Göttingen, Göttingen, Germany (1997)

    Google Scholar 

  27. Yamato, T., Zhang, F.L., Kumamaru, K., yamamoto, K.: Synthesis, conformational studies and inclusion properties of tetrakis[(2-pyridylmethyl)oxy]thiacalix[4]arenes. J. Incl. Phenom. Macro. Chem. 42, 51–60 (2002)

    Article  CAS  Google Scholar 

  28. Lamartine, R., Bavoux, C., Vocanson, F., Martin, A., Senlisb, G., Perrinb, M.: Synthesis, X-ray crystal structure and complexation properties towards metal ions of new thiacalix[4]arenes. Tetrahedron Lett. 42, 1021–1024 (2001)

    Article  CAS  Google Scholar 

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Acknowledgments

We are grateful to the National Natural Science Foundation of China (20772092) and the Hubei Province Natural Science fund for Distinguished Yong Scholars for financial support. We also thank National Laboratory for Optoelectronics, Huazhong University of Science and Technology for support of this research.

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Correspondence to Shu-Ling Gong.

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Li, X., Gong, SL., Yang, WP. et al. Aminopyridyl derivative of thiacalix[4]arene-carboxylic acid as ionizable highly selective Ag+ ionophore. J Incl Phenom Macrocycl Chem 66, 179–184 (2010). https://doi.org/10.1007/s10847-009-9684-9

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  • DOI: https://doi.org/10.1007/s10847-009-9684-9

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