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Synthesis and cation complexation of calix[4]azacrowns and a spirobiscalix[4]azacrown

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Abstract

The synthesis and complexation properties of three new derivatives, one spirobiscalix[4]azacrown (1) and two calix[4]azacrown (2 and 3), are reported. Complexation studies of the three ligands toward transition and heavy metal cations have been carried out and monitored by UV absorption spectrophotometry in acetonitrile. Mononuclear complexes were detected for all complexes, whereas binuclear species (M2L) were also formed in the case of ligand 1 with Cu2+ and Pb2+. The extraction properties of 1, 2 and 3 toward Cu2+, Zn2+, Pb2+, Ag2+ and Cd2+ are also reported. The results showed that complexation is the main factor affecting extraction with ligands 2 and 3, while with ligand 1 it is not.

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References

  1. Lehn, J.-M.: Supramolecular chemistry, concepts and perspectives. Wiley-VCH, New York (1995)

    Book  Google Scholar 

  2. Lehn, J.-M.: Toward self-organization and complex matter. Science. 295, 2400–2403 (2002). and references cited therein

    Article  CAS  Google Scholar 

  3. Alfieri, C., Dradi, E., Pochini, A., Ungaro, R., Andreetti, G.D.: Synthesis and X-ray crystal and molecular structure of a novel macro-bicyclic ligand: crowned p-t-butyl-calix[4]arene. J. Chem. Soc. Chem. Commun. 19, 1075–1077 (1983)

    Article  Google Scholar 

  4. Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J. (eds.): Calixarenes 2001, pp. 365–384. Kluwer Academic Publishers, Dordrecht (2001)

    Google Scholar 

  5. Oueslati, I.: Calix(aza)crowns: synthesis, recognition, and coordination. A mini review. Tetrahedron 63, 10840–10851 (2007)

    Article  CAS  Google Scholar 

  6. Ostaszewski, R., Stevens, T.W., Verboom, W., Reinhoudt, D.N., Kaspersen, F.M.: Calix (aza-)crowns as potential ionophores for divalent and trivalent cations. Recl. Trav. Chim. Pays Bas. 110, 294–298 (1991)

    Article  CAS  Google Scholar 

  7. Oueslati, I., Abidi, R., Thuéry, P., Vicens, J.: Complexation studies of a calix[4](aza)crown and crystal structure of its magnesium complex. J. Inclusion Phenom. Macrocycl. Chem. 47, 173–178 (2003)

    Article  CAS  Google Scholar 

  8. Oueslati, I., Sa Ferreira, R.A., Carlos, D.L., Baleizao, C., Berberan-Santos, M.N., de Castro, B., Vicens, J., Pischel, U.: Calix[4]azacrowns as novel molecular scaffolds for generation of visible and near-infrared lanthanide luminescence. Inorg. Chem. 45, 2652–2660 (2006)

    Article  CAS  Google Scholar 

  9. Oueslati, I., Thuéry, P., Shkurenko, O., Suwinska, K., Harrowfield, J.M., Abidi, R., Vicens, J.: Calix[4]azacrowns: self-assembly and effect of chain length and O-alkylation on their metal ion-binding properties. Tetrahedron 63, 62–70 (2007)

    Article  CAS  Google Scholar 

  10. Hamdi, A., Lee, Y.H., Kim, Y., Kusumahustuti, D.K.A., Ohto, K., Abidi, R., Vicens, J.: A spirobiscalix[4]azacrown: synthesis and complexing properties. Tetrahedron Lett. 50, 540–543 (2009)

    Article  CAS  Google Scholar 

  11. Li, J., Zhong, Z., Chen, Y., Lu, X.: A novel type of double-calixcrown: Spirobiscalix[4]crowns. Tetrahedron Lett. 39, 6507–6510 (1998)

    Article  CAS  Google Scholar 

  12. Li, J.S., Chen, Y.Y., Lu, X.R.: Syntheses of novel tripodal calix[n]cryptands (n = 4, 6) and their extraction abilities toward cations. Eur. J. Org. Chem. 3, 485–490 (2000)

    Article  Google Scholar 

  13. Shi, Z.Q., Feng, Y.Q., Wang, W.X., Wang, H.W.: The synthesis of a N-spirocalixazacrown has been described. Chin. Chem. Lett. 18, 912–914 (2007)

    Article  CAS  Google Scholar 

  14. Unob, F., Asfari, Z., Vicens, J.: An anthracene-based fluorescent sensor for transition metal ions derived from calix[4]arene. Tetrahedron Lett. 39, 2951–2954 (1998)

    Article  CAS  Google Scholar 

  15. Oueslati, I., Abidi, R., Amri, H., Thuéry, P., Nierlich, M., Asfari, Z., Harrowfield, J., Vicens, J.: Cation- and solvent-induced conformational changes of 25, 27-dimethoxy-26, 28-dimethylester-p-tert-butylcalix[4]arene. Tetrahedron Lett. 41, 8439–8443 (2000)

    Article  CAS  Google Scholar 

  16. Lee, Y.H., Mora, C., Choi, J.Y., Byun, J.C., Harrowfield, J.M., Thuéry, P., Kim, Y.: Pentaerythritol fragmentation during conversion to a polyamine ligand—isolation of 1,1-bis(2′-aminoethylaminomethyl)-ethene. Tetrahedron Lett. 51, 4915–4917 (2010)

    Article  CAS  Google Scholar 

  17. Adil, K., Goreshnik, E., Courant, S., Dujardin, G., Leblanc, M., Maisonneuve, V.: Synthesis and structures of new hybrid fluorides templated by tetraprotonated pentaerythrityl tetramine. Solid State Sci. 6, 1229–1235 (2004)

    Article  CAS  Google Scholar 

  18. Turonek, M.L., Moore, P., Clase, H.J., Alcock, N.W.: Synthesis and co-ordination chemistry of the pyridyl pendant-arm azamacrocycles 1-(2-pyridylmethyl)-1, 5, 9-triazacyclododecane L1 and 1-(2-pyridyl-2′-ethyl)-1, 5, 9-triazacyclododecane L2, with nickel (II), copper(II) and zinc(II). Crystal structures of [Ni(L1)(O2NO)]NO3 and [ZnL2][Zn(NO3)3.67Cl0.33]. J. Chem. Soc. Dalton Trans. 22, 3659–3666 (1995)

    Article  Google Scholar 

  19. Pedersen, C.: New macrocyclic polyethers. J. Am. Chem. Soc. 92, 391 (1970)

    Article  CAS  Google Scholar 

  20. Frensddorff, H.K.: Salt complexes of cyclic polyethers. Distribution equilibria. J. Am. Chem. Soc. 93, 4684 (1971)

    Article  Google Scholar 

  21. Sillen, L.G., Warnquist, B.: High speed computers as a supplement to graphical methods. Ark. Kemi. 31, 377–390 (1968)

    Google Scholar 

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Acknowledgments

This research was supported by the National Research Foundation of Korea (Grant 2010-00275) and Kosin University (2010).

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Authors and Affiliations

  1. Faculté des Sciences de Bizerte, LACReSNE, 7021, Zarzouna, Bizerte, Tunisia

    Abdelwaheb Hamdi, Mohamed Habib Noomen & Rym Abidi

  2. Department of Chemistry and Advanced Materials, Kosin University, 149-1, Dongsam-dong, Yeongdo-gu, Busan, 606-701, South Korea

    A. Rim Woo, Jeong Hwan Cho & Yang Kim

Authors
  1. Abdelwaheb Hamdi
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  2. Mohamed Habib Noomen
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  3. Rym Abidi
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  4. A. Rim Woo
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  5. Jeong Hwan Cho
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  6. Yang Kim
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Correspondence to Rym Abidi.

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Dedicated to Professor Leonard F. Lindoy, a great chemist, on the occasion of his 75th birthday.

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Hamdi, A., Noomen, M.H., Abidi, R. et al. Synthesis and cation complexation of calix[4]azacrowns and a spirobiscalix[4]azacrown. J Incl Phenom Macrocycl Chem 71, 287–291 (2011). https://doi.org/10.1007/s10847-011-0029-0

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