Synthesis and receptor properties of calix[4]arene–bisphenol-A copolymers

Abstract

The synthesis of 1,3-dimethyl calix[4]arene–bisphenol-A copolyethers and copolyesters with variable amounts of the macrocycle in the chain is described; the receptor ability of the copolyethers 4 toward silver(I) ions was one hundred-fold that of calix[4]arene tetrapropyl ether 3.

References

1. For recent reviews, see V. Böhmer, Angew. Chem., Int. Ed. Engl., 1995, 34, 713; M. Takeshita and S. Shinkai, Bull. Chem. Soc. Jpn., 1995, 68, 1088; C. D. Gutsche, Aldrichim. Acta, 1995, 28, 3; A. Pochini and R. Ungaro, Comprehensive Supramolecular Chemistry, Pergamon, Oxford, 1996.
2. S. Shinkai, H. Kawaguchi and O. Manabe, J. Polym. Sci., Polym. Lett., 1988, 26, 391; S. J. Harris, G. Barrett and M. A. McKervey, J. Chem. Soc., Chem. Commun., 1991, 1224; J. D. Glennon, K. O'Connor, S. Srijaranai, K. Manley, S. J. Harris and M. A. McKervey, Anal. Lett., 1993, 26, 153.
3. Z.-L. Zhong, C.-P. Tang, C.-Y. Wu and Y.-Y. Chen, J. Chem. Soc., Chem. Commun., 1995, 1737.
4. M. A. McKervey and M. Pitarch, Chem. Commun., 1996, 1689.
5. D. M. Gravett and J. E. Guillet, Macromolecules, 1996, 29, 617.
6. D. W. M. Arrigan, G. Svehla, S. J. Harris and M. A. McKervey, Electroanalysis, 1995, 6, 97; D. Diamond and M. A. McKervey, Chem. Soc. Rev., 1996, 15.
7. W. F. Nijenhuis, E. G. Buitenhuis, F. De Jong, E. J. R. Sudhölter and D. N. Reinhoudt, J. Am. Chem. Soc., 1991, 113, 7963.
8. S. D. Pastor and P. Odorisio, USP 4617336/ 1986(Chem. Abstr. 1987, 106, 6038x); K. Seiffarth, M. Schulz, G. Görmar and J. Bachmann, Poly. Deg. Stab., 1989, 24, 73.
9. For recent work of two of us in the synthesis of carbohydrate containing calix[4]arene, see A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari and R. Ungaro, Angew. Chem., Int. Ed. Engl., 1994, 33, 2479; A. Marra, A. Dondoni and F. Sansone, J. Org. Chem., 1996, 61, 5155.
10. A. Ikeda, T. Nagasaki, K. Araki and S. Shinkai, Tetrahedron, 1992, 48, 1059.
11. For examinations of calixarene-based ionophores with this procedure, see ref. 3 and C. A. Gleave and I. O. Sutherland, J. Chem. Soc., Chem. Commun., 1994, 1873.
12. J. M. Timko, S. S. Moore, D. M. Walba, P. C. Hiberty and D. J. Cram, J. Am. Chem. Soc., 1977, 99, 4207; S. S. Moore, T. L. Tarnowski, M. Newcomb and D. J. Cram, J. Am. Chem. Soc., 1977, 99, 6398; G. M. Lein and D. J. Cram, J. Am. Chem. Soc., 1985, 107, 448.
13. A. Ikeda, H. Tsuzuki and S. Shinkai, J. Chem. Soc., Perkin Trans. 2, 1994, 2073.