Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Synthesis and properties of calix[4]crown-6 functionalized polymers

  • 67 Accesses

  • 10 Citations


Calix[4]crown-6-2,4-bis(4-aminobutyl ether), which has a crown-6 moiety at the 1,3-position and amino function at the 2,4-position, was prepared as an intermediate for the subsequent synthesis of calix[4]crown-6-containing polyamide and polyimide using adipoyl chloride and 1,2,4,5-benzenetetracarboxylic dianhydride. The chemical structures were characterized by IR,1H NMR spectroscopy and elemental analysis, and some of their physical properties, including their thermal behavior, were examined. The ion binding characteristics of the monomer and polymers for alkali metal and alkali earth metal ions were measured by liquid-liquid extraction from the aqueous phase into the organic phase. It has been observed that polyamide has a high binding ability towards various metal cations as compared to polyimide, which showed cesium ion selectivity.

This is a preview of subscription content, log in to check access.


  1. (1)

    A. Castini, R. Ungaro, Z. Asfari, J. Vicens, in Calixarenes 2001, Z. Asfari, V. Böhmer, J. Harrowfield, and J. Vicens, Eds., Kluwer Academic, Dordrecht, 2001.

  2. (2)

    L. Nicod, S. Pellet-Rostaing, F. Chitry, and M. Lemaire,Tetrahedron,39, 9443 (1998).

  3. (2)

    J. S. Kim, W. K. Lee, W. B. Sim, J. W. Ko, M. H. Cho, D. Y. Ra, and J. W. Kim,J. Inc. Phe. Mac. Chem.,37, 359 (2000).

  4. (3)

    J. S. Kim, O. J. Shon, W. B. Sim, S. K. Kim, M. H. Cho, J. G. Kim, I. H. Suh, and D. W. Kim,J. Chem. Soc., Perkin Trans.,1, 31 (2001).

  5. (4)

    J. S. Kim, P. Thuery, M. Nierlich, J. A. Rim, S. H. Yang, J. K. Lee, K. H. Cho, J. H. Lee, and J. Vicens,Bull. Korean Chem. Soc.,22, 321 (2001).

  6. (5)

    N. Reynier, J. F. Dozol, M. Saadioui, Z. Asfari, and J. Vicens,Tetrahedron Lett.,39, 6461 (1998).

  7. (6)

    F. A. Neu and M. J. S. Weill,Syn. Met.,90, 157 (1997).

  8. (7)

    M. Mathieu, Z. Asfari, and J. Vicens,Tetrahedron Lett.,43, 1225 (2002).

  9. (8)

    Z. Asfari, P. Thuery, M. Nierlich, and J. Vicens,J. Tetrahedron Lett.,40, 499 (1999).

  10. (9)

    V. Böhmer, R. Dorrenbacher, M. Frings, M. Heydenreich, D. Paoli, W. Vogt, G. Ferguson, and I. Thondorf,Tetrahedron Lett.,61, 549 (1996).

  11. (10)

    C. P. Jimenés, L. Escriche, and J. Casabó,Analytica Chim. Acta,371, 155 (1998).

  12. (11)

    H. Deligöz and M. Yilmaz,J. Polym. Sci.; Part A: Polym. Chem.,32, 2961 (1994).

  13. (12)

    H. Deligöz and M. Yilmaz,J. Polym. Sci.; Part A: Polym. Chem.,33, 2851 (1995).

  14. (13)

    S. Memon, A. Yilmaz, and M. Yilmaz,J. Polym. Sci.; Part A: Polym. Chem.,37, 4351 (1999).

  15. (14)

    S. Shinkai, H. Kawaguchi, and O. Manabe,J. Polym. Sci.; Part C: Polym. Lett.,26, 391 (1988).

  16. (15)

    D. Gravett and J. E. MGuillet,Macromolecules,29, 617 (1997).

  17. (16)

    K. Ohto, Y. Tanaka, and K. Inoue,Chem. Lett., 647 (1997).

  18. (17)

    J. S. Kim, S. K. Kim, and J. W. Ko,Talanta,52, 1143 (2000).

  19. (18)

    S. Memon, G. Uysal, and M. Yilmaz,React. Funct. Polym.,47, 165 (2001).

  20. (19)

    S. Memon, G. Uysal, and M. Yilmaz,React. Funct. Polym.,50, 77 (2001).

  21. (20)

    H. Deligöz and M. Yilmaz,React. Funct. Polym.,31, 81 (1996).

  22. (21)

    S. Memon, A. Ylmaz, and M. Yilmaz,J. Macromol. Sci.; Part A: Pure and Appl. Chem.,37, 865 (2000).

  23. (22)

    H. Deligöz and M. Yilmaz,Solvent Extr. Ion Exch.,13, 19 (1995).

  24. (23)

    J. S. Kim, M. H. Cho, S. C. Lee, J. H. Pang, J. H. Lee, and A. Ohki,Talanta,49, 69 (1999).

  25. (24)

    J. S. Kim, M. H. Cho, J. H. Cho, R. A. Bartsch, Y. I. Lee, and I. H. Kim,Talanta,51, 99 (2000).

  26. (25)

    W. H. Seol, S. H. Kim, C. W. Lee, and M. S. Gong,Bull. Korean Chem. Soc.,25, 1265 (2004).

  27. (26)

    Y. S. Yang, W. H. Seol, C. W. Lee, and M. S. Gong,Macromol. Res.,12, 427 (2004).

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Kim, S., Lee, C., Jeon, Y. et al. Synthesis and properties of calix[4]crown-6 functionalized polymers. Macromol. Res. 13, 141–146 (2005). https://doi.org/10.1007/BF03219028

Download citation


  • calix[4]crown-6
  • polyamide
  • polyimide
  • ion-binding