Calix[4]arenes with perfluorinated alcoholic functions at the upper rim: a new class of neutral anion receptors

Abstract

Two or four perfluorinated alcoholic functions were successfully introduced at the upper rim of calix[4]arenes, affording a new type of neutral receptor for anion recognition; preliminary binding studies indicate that the difunctionalized receptors 3a and 3b are selective for Y-shaped carboxylate ions over spherical anions which are, on the contrary, more efficiently bound by the tetraalcohol 6.

References

1. Supramolecular Chemistry of Anions, ed. A. Bianchi, K. Bowman-James, E. Garcia-España, Wiley, New York, 1997; P. D. Beer and P. Schmitt, Curr. Opin. Chem. Biol., 1997, 1, 475; F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609; M. M. G. Antonisse and D. N. Reinhoudt, Chem. Commun., 1998, 443.
2. B. Dietrich, T. M. Fyles, J. M. Lehn, L. G. Pease and D. L. Fyles, J. Chem. Soc., Chem. Commun., 1978, 934.
3. P. D. Beer, Chem. Commun., 1996, 689; M. P. Hughes and B. D. Smith, J. Org. Chem., 1997, 62, 4492.
4. P. Bühlmann, S. Nishizawa, K. P. Xiao and Y. Umezawa, Tetrahedron Lett., 1997, 53, 1647.
5. For a recent Review Article on amides in anion recognition, see I. Stibor, D. S. M. Hafeed, P. Lhoták, J. Hodacová, J. Koca and M. Cajan, Gazz. Chim. Ital., 1997, 127, 673; B. R. Cameron and S. J. Loeb, Chem. Commun., 1997, 573.
6. (a) J. Scheerder, M. Fochi, J. F. J. Engbersen and D. N. Reinhoudt, J. Org. Chem., 1994, 59, 7815; (b) A. Casnati, M. Fochi, P. Minari, A. Pochini, M. Reggiani, R. Ungaro and D. N. Reinhoudt, Gazz. Chim. Ital., 1996, 126, 99; (c) N. Pelizzi, A. Casnati, A. Friggeri and R. Ungaro, J. Chem. Soc., Perkin Trans. 2, 1998, 1307.
7. M. Fe de la Torre, S. Gonzales, E. G. Campos, M. L. Mussons, J. R. Moran and M. Cruz Caballero, Tetrahedron Lett., 1997, 38, 8591.
8. C. Reichardt, Solvents and Solvent Effects in Organic Chemistry, VCH, Weinheim, 1988.
9. F. L. Schadt, P. v. R. Schleyer and T. W. Bentley, Tetrahedron Lett., 1974, 27, 2335.
10. W. H. Pirkle, R. L. Muntz and I. C. Paul, J. Am. Chem. Soc., 1971, 93, 2817; W. H. Pirkle and P. L. Rinaldi, J. Org. Chem., 1977, 42, 3217.
11. X. Creary, J. Org. Chem., 1987, 52, 5026; L. S. Chen, G. J. Chen and C. Tamborski, J. Fluorine Chem., 1981, 18, 117.
12. A. Dondoni, A. Marra, M. —C. Scherrmann, A. Casnati, F. Sansone and R. Ungaro, Chem. Eur. J., 1997, 3, 1774.
13. R. Krishanamurti, D. R. Bellew and G. K. S. Prakash, J. Org. Chem., 1991, 56, 984; G. K. S. Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757.
14. J. Scheerder, R. Vreekamp, J. F. J. Engbersen, W. Verboom, J. P. M. van Duynhoven and D. N. Reinhoudt, J. Org. Chem., 1996, 61, 3476; O. Mogck, E. F. Paulus, V. Böhmer, I. Thondorf and W. Vogt, Chem. Commun., 1996, 2533.
15. F. Sansone, S. Barboso, A. Casnati, M. Fabbi, A. Pochini, F. Ugozzoli and R. Ungaro, Eur. J. Org. Chem., 1998, 897.
16. T. R. Kelly and M. H. Kim, J. Am. Chem. Soc., 1994, 116, 7072; P. J. Smith, H. V. Reddington and C. Wilcox, Tetrahedron Lett., 1992, 33, 6085.