Synthesis and Selective Extractant Properties of a Calixarene Thioether Derivative and its Oligomeric Analogue
Herein we report the synthesis of a novel calix[4]arene thioether derivative (4) and its oligomeric analogue (5). The liquid-liquid extraction properties of these compounds towards the selected metal cations were evaluated, and it was concluded, based on our observations, that these compounds demonstrated remarkable affinity towards the selected metal cations. Nevertheless, is a good extractant and very selective for Hg2+ ions, whereas, in the case of its oligomeric analogue 5, the situation is quiet different. It was observed that 5 could not efficiently retain the parent selective behavior by extracting all of the selected metal ions from the aqueous to the organic phase.
Synthesis and Selective Extractant Properties of a Calixarene Thioether Derivative and its Oligomeric Analogue
Herein we report the synthesis of a novel calix[4]arene thioether derivative (4) and its oligomeric analogue (5). The liquid-liquid extraction properties of these compounds towards the selected metal cations were evaluated, and it was concluded, based on our observations, that these compounds demonstrated remarkable affinity towards the selected metal cations. Nevertheless, is a good extractant and very selective for Hg2+ ions, whereas, in the case of its oligomeric analogue 5, the situation is quiet different. It was observed that 5 could not efficiently retain the parent selective behavior by extracting all of the selected metal ions from the aqueous to the organic phase.
___
- C.D. Gutsche, “Calixarenes Revisited”, The Royal Society of Chemistry, Cambridge, 1998.
- S.I. Kim, T.J. Shin, M. Ree, G.T. Hwang, B.H. Kim, H. Han, J. Polym. Sci. Part A: Polym. Chem. 37, 2026 (1999).
- J. Vicens, and V. Bohmer, “Calixarenes: A Versatile Class of Macrocyclic Compounds Topics in Inclusion Science”, Kluwer Academic Publishers: Dordrecht, 1991.
- N. Singh, M. Kumar, G. Hundal, Tetrahedron 60, 5393-5405 (2004).
- Z-L. Zhong, C-P. Tang, C-Y. Wu, Y-Y. Chen, J. Chem. Soc. Chem. Commun. 1737-1738 (1995).
- E. Kocabas, A. Karakucuk, A. Sirit, M. Yilmaz, Tetrahedron: Asymmetry 17, 1514-1520 (2006).
- S. Patra, E. Suresh and P. Paul, Polyhedron 26, 4971-4980 (2007)
- T. Hascall, K. Pang and G. Parkin, Tetrahedron 63, 10826-10833 (2007).
- A. Demirel, A. Dogan, G. Akku¸s M. Yilmaz, and E. Kılıc, Electroanalysis 18, 1019-1027 (2006).
- V. Csokai, A. Gr¨un, B. Bal´azs, A. Simon, G. T´oth and I. Bitter, Tetrahedron 62, 10215-10222 (2006).
- S. Bozkurt, A. Karakucuk, A. Sirit, M. Yilmaz, Tetrahedron 61, 10443-10448 (2005).
- Y. H. Kim, N. R. Cha and S.-K. Chang, Tetrahedron Lett. 43, 3883-3886 (2002).
- O. Ediz, M. Tabakci, S. Memon, M. Yilmaz, D. M. Roundhill, Supramol. Chem. 16, 199–204 (2004). ¨
- S. Tanaka, H. Katagiri, N. Morohashi, T. Hattori and S. Miyano, Tetrahedron Lett. 48, 5293-5296 (2007).
- M. Tabakci, S. Memon, M. Yilmaz, D. M. Roundhill, J. Incl. Phenom. Macrocycl Chem. 45, 267-270 (2003).
- M. Tabakci, S. Memon, M. Yilmaz, Tetrahedron 63, 6861-6865 (2007).
- A.T. Yordanov, D.M. Roundhill, New J. Chem. 20, 447-451 (1996).
- M. Tabakci, S. Memon, B. Sap, D.M. Roundhill, M. Yilmaz, J. Macromol. Sci. Part A-Pure and App. Chem. 41, 811-825 (2004).
- M. Tabakci, S. Memon, M. Yilmaz, D.M. Roundhill, J. Polym. Sci. Part A: Polym. Chem. 42, 186-193 (2004).
- H.K. Alpoguz, S. Memon, M. Ersoz, M. Yilmaz, Sep. Sci. Technol. 39, 799-810 (2004).
- H.K. Alpo˘guz, S. Memon, M. Ers¨oz, M. Yilmaz, Sep. Sci. Technol. 38, 1649-1664 (2003).
- S. Memon, G. Uysal, M. Yilmaz, Sep. Sci. Technol. 35, 1247-1256 (2000).
- H.K. Alpoguz, S. Memon, M. Ers¨oz, M. Yilmaz, New J. Chem. 26, 477-480 (2002).
- S. Shinkai, H. Kawaguchi and O. Manabe, J. Pol. Sci. Part C: Polymer Lett. 26, 391-396 (1988).
- S.J. Harris, G. Barrett, M.A. McKervey, J. Chem. Commun. 1224-1225 (1991).
- D.M. Gravett, and J.E. Guillet, Macromolecules 29, 617 -624 (1996).
- Z.-L. Zhong, C.-P. Tang, C.-Y. Wu, and Y.-Y. Chen, J. Chem. Soc., Chem. Commun. 1737-1738 (1995).
- K. Ohto, Y. Tanaka, and K. Inoue, Chem. Lett. 7, 647-648 (1997).
- M. Blanda, and E. Adou, Polymer 39, 3821-3826 (1998).
- S. Memon, M. Tabakci, D.M. Roundhill, and M. Yilmaz, Reactive and Funct. Polym. 66, 1342-1349 (2006).
- M. Tabakci, M. Ers¨oz, and M. Yilmaz, J. Macromol. Sci., Part A: Pure and Appl. Chem. 43, 1–13 (2006).
- G. Uysal, S. Memon M. Yilmaz, React. Funct. Polym. 50, 77-84 (2001).
- S. Memon, G. Uysal, M. Yilmaz, React. Funct. Polym. 47, 165-174 (2001).
- S. Memon, A. Yilmaz, D.M. Roundhill, M. Yilmaz, J. Macromol. Sci. Part A: Pure Appl. Chem. , 435–449 (2004).
- S. Memon, A. Yilmaz, and M. Yilmaz, J. Macromol. Sci. Part A: Pure Appl. Chem. 37, 865-879 (2000).
- G. Uysal Akkus, S. Memon, D. Erol Gurkas, S. Aslan, M. Yilmaz, React. and Funct. Polym. 68, 125-132 (2008).
- S. Erden, A. Demirel, S. Memon, M. Yilmaz, E. Canel, and E. Kılı¸c Sensors and Actuators B 113, 290–296 (2006)
- C.D. Gutsche, M. Iqbal, Org. Syn. 68, 234-235 (1990).
- M. Tabakci, S. Memon, M. Yilmaz, D.M. Roundhill, React. Funct. Polym. 58, 27-34 (2004).
- S. Memon, M. Tabakci, D.M. Roundhill, M. Yilmaz, Polymer 46, 1553-1560 (2005).
- J. Pedersen, Am. Soc. Exp. Biol. 27, 1305-1309 (1968)
- G. Uysal Akku¸s, S. Memon, and M. Yilmaz, Polycycl. Arom. Comp. 22, 1075-1086 (2002).
- V.S. Talanov, E.D. Roper, N.M. Buie, G.G. Talanova, Tetrahedron Lett. 48, 8022-8025 (2007).
- R.G. Pearson, J.Am. Chem. Soc. 85, 3533-3534 (1963).
- A. Yilmaz, M. Yilmaz, R.A. Bartsch, J. Macromol. Sci., Part A: Pure Appl. Chem. 43, 1-9 (2006).