Gülsen ASMAN, Muhammad ASHRAM, Nawash AL-GHEZAWI, Ibrahim Abu AWAAD

Synthesis and physical studies of polycarbonate of p-tert-butylcalix[4]arena: a highly selective receptor for $Na^+$

The synthesis and characterization of a polycarbonate of p-tert-butylcalix[4]arene 4 are reported. It was synthesized by condensation of p-tert-butylcalix[4]arenetetraol derivative 3 with ethyl chloroformate. This new polymer possesses a hydrolyzable backbone and tunable hydrophobic/hydrophilic properties. The experimental results indicate that the polycarbonate was successfully synthesized with average molecular weight Mw , (2.328 × 104 g/mol), which was determined by static light scattering method using a Berry plot. The structure of this polymer was determined by IR spectroscopy. The thermal properties were investigated using differential scanning calorimetry (DSC). The degree of crystallinity was measured by means of XRD. The extraction ability of compounds 3 and 4 toward alkali metal cations was studied using conductometry. It was observed that compound 4 had the highest extractability and selectivity toward Na+.

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1. Vicens, J.; B¨ohmer, V. Calixarenes: A Versatile Class of Macrocyclic Compounds; Kluwer: Dordrecht, 1991.
2. Asfari, Z.; B¨ohmer, V.; Harroweld, J.; Vicens, J. (Eds.), Calixarenes 2001, Kluwer Academic Publishers, Dordrecht.
3. Kim, J. S.; Shon, O. J.; Sim, W. B.; Kim, S. K.; Cho, M. H.; Kim, J. G.; Suh, I. H.; Kim, D. W. J. Chem. Soc., Perkin Trans. 1, 2001, 31-36.
4. Kim, J. S.; Thuery, P.; Nierlich, M.; Rim, J. A.; Yang, S. H.; Lee, J. K.; Cho, K. H., Lee, J. H.; Vicens, J. Bull. Korean Chem. Soc. 2001, 22, 321-324.
5. Vicens, J.; B¨ohmer, V.; Calixarenes: A Versatile Class of Macrocyclic Compounds Topics in Inclusion Science, Kluwer Academic Publishers, Dordrecht, 1991.
6. Mathieu, M.; Asfari, Z.; Vicens, J.; Tetrahedron Lett. 2002, 43, 1225-1229.
7. Kim, J. S.; Yu, S. H.; Cho, M. H.; Shon, O. J.; Rim, J. A.; Yang, H.; Lee, J. K.; Lee, S. J. Bull. Korean Chem. Soc. 2001, 22, 519-522.
8. Sugiura, M. Sep. Sci. Tech. 1990, 25, 1189-1199.
9. Blanda, M. T.; Adou, E. Chem. Commun. 1998, 139-140.
10. Dondoni, A.; Ghiglione, C.; Marra, A.; Scoponi, M. Chem. Commun. 1997, 673-674.
11. Harris, S. J.; Barrett, G.; McKervey, M. A. J. Chem. Commun. 1991, 1224-1225.
12. Delig¨oz, H. and Yilmaz, M. J. Polym. Sci. Part A: Polym. Chem. 1995, 33, 2851-2853.
13. Yilmaz, M. React. Funct. Polym. 1999, 40, 129-133.
14. Gravett, D.;.; Guillet, J. E. Macromolecules 1996, 29, 617-624.
15. Lanza, R. P.; Langer, R.; Chick, W. L. Principles of Tissue Engineering, R.G. Landes/Academic Press: San Diego, CA, 1997.
16. Ratner, B. D.; Hoffman, A. S.; Schoen, F. J.; Lemons, J. E. Biomaterials Science: An Introduction to Material in Medicine, Academic Press: San Diego, 2000.
17. Griffith, L. G.; Naughton, G. Science, 2002, 295, 1009-1014.
18. Zhou, Q. J.; Kohn, K. Macromolecules 1990, 23, 3399-3406.
19. Gelbin, M. E.; Kohn, J. J. Am. Chem. Soc. 1992, 114, 3962-3965.
20. Kimura, Y.; Shirotani, K.; Yamane, H.; Kitao, T. Macromolecules 1988, 21, 3338-3340.
21. Tian, D.; Dubois, P.; Grandfils, C. J´erˆome, R. Macromolecules 1997, 30, 406-409.
22. Barrera, D. A.; Zylstra, E.; Lansbury, P. T.; Langer, R. J. Am. Chem. Soc. 1993, 115, 11010-11011.
23. Barrera, D. A.; Zylstra, E.; Lansbury, P. T.; Langer, R. Macromolecules 1995, 28, 425-432.
24. Elisseeff, J.; Anseth, K.; Langer, R.; Hrkach, J. S. Macromolecules 1997, 30, 2182-2184.
25. Carnahan, M. A.; Grinstaff, M. W. J. Am. Chem. Soc. 2001, 123, 2905-2906.
26. Carnahan, M. A.; Grinstaff, M. W. Macromolecules 2001, 34, 7648-7655.
27. Carnahan, M. A.; Middleton, C.; Kim, J.; Kim T.; Grinstaff, M. W. J. Am. Chem. Soc. 2002, 124, 5291-5293.
28. Kojimai, T.; Nakano, M.; Juni, K.; Inoue, S.; Yoshida, Y. Chem. Pharm. Bull. 1984, 32, 2795-2802.
29. Wang, H.; Dong, K.; Gu, Z. J. Polym. Sci., Part A: Polym. Chem. 1998, 36, 1301-1307.
30. Arnaud-Neu, F.; Collins, E. M.; Deasy, M.; Ferguson, G.; Harris, S. J.; Kaitner, B.; Lough, A. J.; McKervey, M. A.; Marques, E.; Ruhl, B. L.; Schwing-Weill, M. J.; Seward, E. M. J. Am. Chem. Soc. 1989, 111, 8681-8691.
31. Tabakci, M.; Tabakci, B.; Yilmaz, M. J. Incl. Phenom. Macrocycl. Chem. 2005, 53, 51-56.
32. Moran, J. K.; Georgive, E. M.; Yordanov, A. T.;Mague, J. T.; Roundhill, D. M. J. Org. Chem. 1994, 59, 5990-5998.
33. Berti, C.; Bonora, V.; Fiorini, M.; Pilati, F.; Sweileh, B. Macromol. Chem. and Phys. 1997, 198, 321-328.
34. Kricheldorf, H. R.; Schwarz G. Makromol. Chem. 1983, p:184+475.
35. Montaudo, G.; Puglisi, C.; Samperi, F. Polym. Degrad. Stabil. 1991, 31 (3), 291-326.