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Synthesis and characterization of three novel azocalix[4]arene Schiff base derivatives and their selective copper extraction

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Abstract

The synthesis and characterization of three novel Schiff bases of azocalix[4]arene and their selective copper extraction are described. The preparation of azocalix[4]arenes (1c, 2c and 3c) has been achieved by the condensation of 2-hydroxy-3-methoxybenzaldehyde with the amine group of upper rim mono-, di- and tetra-(aminophenylazo) calix[4]arene in ethanol. The synthesized products (1c, 2c and 3c) are characterized by both 1H and 13C NMR techniques, IR spectroscopy and elemental analysis. Extraction capabilities of interested derivatives of azocalix[4]arene from aqueous phase into organic phase are also examined. While extraction of Ag+, Hg+ and Hg2+ cations gave strong complexes with azo groups, extraction of Cu2+ cation is found to be highly effective with –CH=N– and neighboring –OH groups.

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References

  1. C.D. Gutsche, J.F. Stoddart, in Calixarenes revisited. Monographs in supramolecular chemistry (The Royal Society of Chemistry, London, 1998), p.149–167

  2. M. Durmaz, S. Alpaydın, A. Sırıt, M. Yilmaz, Chiral Schiff base derivatives of calix[4]arene: synthesis and complexation studies with chiral and achiral amines. Tetrahedron Asymmetr. 17, 2322–2327 (2006)

    Article  CAS  Google Scholar 

  3. H. Deligöz, Azocalixarenes: synthesis, characterization, complexation, extraction, absorption properties and thermal behaviours. J. Incl. Phenom. Macrocyclic Chem., 55, 197–218 (2006) (Review article)

    Google Scholar 

  4. H.M. Chawla, S.P. Singh, S.N. Sahu, S. Upreti, Shaping the cavity of calixarene architecture for molecular recognition: Synthesis and conformational properties of new azocalix[4]arenes. Tetrahedron 62, 7854–7865 (2006a)

    Article  CAS  Google Scholar 

  5. H.M. Chawla, S.P. Singh, S. Upreti, Synthesis of cesium selective pyridyl azocalix[n]arenes. Tetrahedron 62, 2901–2911 (2006b)

    Article  CAS  Google Scholar 

  6. H. Deligöz, N. Ercan, The synthesis of some new derivatives of calix[4]arene containing azo groups. Tetrahedron 58(14), 2881–2884 (2002)

    Article  Google Scholar 

  7. H. Deligöz, Synthesis and properties of a series of novel calix[6]arene diazo derivatives. J. Incl. Phenom. Macrocycl. Chem. 43(3/4), 285–289 (2002)

    Article  Google Scholar 

  8. H. Shimuzu, K. Iwamoto, K. Fujimoto, S. Shinkai, Chromogenic calix[4]arene. Chem. Lett. 2147–2150 (1991)

  9. A.A. Alemi, B. Shaabani, Synthesis and characterization of a Schiff base of p-tert-butylcalix [4]arene and its complex with copper(II). Acta Chim. Slov. 47, 363–367 (2000)

    CAS  Google Scholar 

  10. M.A. Phaniband, P.G. Avaji, S.D. Dhumwad, Synthesis, spectral characterization and biological evaluation of some lanthanite(III) complexes of Schiff bases of carbostyril derivatives”. Main Group Chem. 7(4), 271–283 (2008)

    Article  CAS  Google Scholar 

  11. N.H. Patel, H.M. Parekh, M.N. Patel, Synthesis, physicochemical characteristics and biocidal activity of some transition metal mixed-ligand complexes with bidentate (NO and NN) Schiff bases. Pharma. Chem. J. 41(2), 78–81 (2007)

    Article  CAS  Google Scholar 

  12. H. Deligöz, M.S. Ak, Azocalixarenes.6: synthesis, complexation, extraction and thermal behaviour of four new azocalix[4]arene. J. Incl. Phenom. Macrocycl. Chem. 59, 115–123 (2007)

    Article  Google Scholar 

  13. Ö.Ö. Karakuş, H. Deligöz, Azocalixarenes.8: synthesis and investigation of the absorption spectra of di-substituted azocalix[4]arenes containing groups. J. Incl. Phenom. Macrocycl. Chem. 61, 289–296 (2008)

    Article  Google Scholar 

  14. Ö.Ö. Karakuş, H. Deligöz, Azocalixarenes7: synthesis and study of the absorption properties of novel mono-substituted chromogenic azocalix[4]arenes. Turkish J. Chem. 35, 87–98 (2011)

    Google Scholar 

  15. H. Deligöz, M. Yilmaz, Liquid–liquid extraction of transition metal cations by calixarenes-based cyclic ligands. Solv. Extr. Ion Exch. 13(1), 19–26 (1995)

    Article  Google Scholar 

  16. H. Deligöz, E. Erdem, Comparative studies on the solvent extraction of transition metal cations by calixarene, phenol and ester derivatives. J. Hazard. Mater. 154(1/3), 29–32 (2008)

    Article  Google Scholar 

  17. J. Lu, X. Tong, X. He, A mercury ion-selective electrode based on a calixarene derivative containing the thiazole azo group. J. Electroanal. Chem. 540, 111–117 (2003)

    Article  CAS  Google Scholar 

  18. J.Y. Kim, C.R. Kim, S.H. Lee, J.H. Lee, J.S. Kim, UV band splitting of chromogenic azo-coupled calix[4]crown upon cation complexation. J. Org. Chem. 68, 1933–1937 (2003)

    Article  CAS  Google Scholar 

  19. V. Arora, H.M. Chawla, T. Francis, M. Nanda, S.P. Singh, Synthesis of a new cesium selective calix[4]arene based chromoionophore. Indian J. Chem. 42, 3041–3043 (2003)

    Google Scholar 

  20. Q. Ma, H. Ma, M. Su, Z. Wang, L. Nie, S. Liang, Determination of nickel by a new chromogenic azocalix[4]arene. Anal. Chim. Acta 439, 73–79 (2001)

    Article  CAS  Google Scholar 

  21. H. Deligöz, Synthesis of an oligomer and a styrene polymer-supported calix[4]arene derivatives and selective extraction of Fe3+. Supramol. Chem. 15(5), 317–321 (2003)

    Article  Google Scholar 

  22. M. Yilmaz, H. Deligöz, Studies on compounds of uranium(VI) with two vic-dioxime derivatives of calix[4]arene. Synth. React. Inorg. Met. Org. Chem. 28(5), 851–861 (1998)

    Article  CAS  Google Scholar 

  23. F. Karcı, I. Şener, H. Deligöz, Azocalixarenes.1: synthesis, characterization and investigation of the absorption spectra of substituted azocalix[4]arenes. Dyes Pigments 59, 53–61 (2003)

    Article  Google Scholar 

  24. H. Deligöz, M. Yilmaz, Synthesis of polymer supported calix[4]arene and selective extraction of Fe3+. React. Funct. Polym. 31, 81–88 (1996)

    Article  Google Scholar 

  25. H. Deligöz, A.I. Pekacar, M.A. Özler, M. Ersöz, Solvent extraction of Fe3+ cation by 25, 26, 27, 28-tetraisonitrosoaceto calix[4]arene and based ligands. Sep. Sci. Technol. 34(16), 3297–3304 (1999)

    Article  Google Scholar 

  26. M. Ak, D. Taban, H. Deligöz, Transition metal cation extraction by ester and ketone derivatives of chromogenic azocalix[4]arene. J. Hazard. Mater. 154(1-3), 51–54 (2008)

    Article  CAS  Google Scholar 

  27. C.D. Gutsche, M. Iqbal, p-tert-butylcalix[4]arene. Org. Synth. 68, 234–238 (1990)

    CAS  Google Scholar 

  28. C.D. Gutsche, M. Iqbal, D. Stewart, Calixarenes.18. Synthesis procedures for para-tert-butylcalix[4]arene. J. Org. Chem. 51, 742–745 (1986)

    Article  CAS  Google Scholar 

  29. C.D. Gutsche, L.G. Lin, Calixarenes 12. The synthesis of functionalized calixarenes. Tetrahedron 42, 1633–1640 (1986)

    Article  CAS  Google Scholar 

  30. C.D. Gutsche, K.A. See, Calixarene.27. Synthesis, characterization and complexation studies of double-cavity calix[4]arenes. J. Org. Chem. 57(16), 4527–4539 (1992)

    Article  CAS  Google Scholar 

  31. Z. Asfari, F. Arnaud-Neu, J. Vicens, Schiff base p-tert-butylcalix[4]arenes. Synthesis and metal ion complexation. J. Org. Chem. 59, 1741–1744 (1994)

    Article  Google Scholar 

  32. B. Dede, F. Karipcin, M. Cengiz, Synthesis, characterization and extraction studies of N,N″-bis[1-biphenyl-2-hydroxyimino-2-(4-acetylanilino)-1-ethylidene]-diamines and their homo-and heteronuclear copper(II) complexes. J. Chem. Sci. 121(2), 163–171 (2009)

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Research Foundation of Pamukkale University, Denizli, Turkey (BAP 2006FEF005), which is gratefully acknowledged for financial assistance.

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  1. Department of Chemistry, Faculty of Science-Arts, Pamukkale University, 20017, Denizli, Turkey

    Özlem Özen Karakuş & Hasalettin Deligöz

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  1. Özlem Özen Karakuş
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  2. Hasalettin Deligöz
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Correspondence to Özlem Özen Karakuş.

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Karakuş, Ö.Ö., Deligöz, H. Synthesis and characterization of three novel azocalix[4]arene Schiff base derivatives and their selective copper extraction. J IRAN CHEM SOC 9, 93–100 (2012). https://doi.org/10.1007/s13738-011-0014-y

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