Abstract
This communication describes the synthesis of Schiff base calix[4]arene (1) in which the Schiff base unit bridges two opposite hydroxy groups ofp-tert-butylcalix[4]arene. The synthesis of (1) has been achieved by refluxing in acetonitrile-methanol the appropriate 1,3-dicarbaldehyde-p-tert-butyl-calix[4]arene (4) with 1,3-diaminopropane. The yield of the reaction is 19%. Ligand (1) possesses a compartment containing two nitrogen atoms, four ether-type oxygen atoms, and two ionizable hydroxy groups likely to complex metal cations.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
C. Alfieri, E. Dradi, A. Pocchini, R. Ungaro, and G. D. Andreetti:J. Chem. Soc., Chem. Commun. 1075 (1983).
R. Ungaro and A. Pocchini: in:Frontiers in Supramolecular Organic Chemistry and Photochemistry, Eds. H.-J. Schneider and H. Dürr, VCH Verlagsgesellschaft, Weinheim (1991), and references therein.
E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A. A. El-Fald, and D. N. Reinhoudt:J. Am. Chem. Soc. 112, 6979 (1990).
Z. Asfari, R. Abidi, F. Arnaud, and J. Vicens:J. Incl. Phenom. 13, 163 (1992).
P. J. Dijkstra, J. A. Brunink, K.-E. Bugge, D. N. Reinhoudt, S. Harkema, R. Ungaro, F. Ugozzoli, and E. Ghidini:J. Am. Chem. Soc. 111, 7567 (1989) and references therein.
P. D. Beer and A. D. Keefe:J. Incl. Phenom. 5, 499 (1987).
J.-D. van Loon, D. Kraft, M. J. K. Ankoné, W. Verboom, S. Harkema, W. Vogt, V. Böhmer, and D. N. Reinhoudt:J. Org. Chem. 55, 5176 (1990).
R. Ostaszewski, T. W. Stevens, W. Verboom, and D. N. Reinhoudt:Rec. Trav. Chim. Pays-Bas 110, 294 (1991).
C. D. Gutsche, M. Iqbal, K. S. Nam, K. A. See, and I. Alam:Pure Appl. Chem. 60, 483 (1988); K. A. See, F. R. Fronezek, W. H. Watson, R. P. Kashyap, and C. D. Gutsche, J. Org. Chem. 56, 7256 (1991).
W. F. Nijenhuis, A. R. van Door, A. M. Reichwein, F. de Jong, and D. N. Reinhoudt:J. Am. Chem. Soc. 113, 3607 (1991).
C. D. Gutsche and M. Iqbal:Org. Syn. 68, 234 (1989).
F. Arnaud-Neu, S. Cremin, D. Cunningham, S. J. Harris, P. McCardle, M. A. McKervey, M. McManus, M. J. Schwing-Weill, and K. Ziat:J. Incl. Phenom. 10, 329 (1991).
D. E. Fenton and P. A. Vigato:Chem. Soc. Rev. 17, 69 (1988).
U. Casellato, P. Guerriero, S. Tamburini, S. Sitran, and P. A. Vigato:J. Chem. Soc. Dalton Trans. 2145 (1991).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Seangprasertkij, R., Asfari, Z., Arnaud, F. et al. A Schiff basep-tent-butylcalix[4]arene. Synthesis and metal ion complexation. J Incl Phenom Macrocycl Chem 14, 141–147 (1992). https://doi.org/10.1007/BF01029661
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01029661