Molecular recognition using β-cyclodextrin-modified dendrimers: novel building blocks for convergent self-assembly

Abstract

The synthesis of β-cyclodextrin-based dendrimers 3 and 5 is described; using phenolphthalein as a UV–VIS active probe, it is shown that the binding cavities of these modified receptors retain their molecular recognition properties and can be employed as polyfunctional monomers in self-assembly.

References

1. G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803.
2. (a) M. L. Bender and M. Komiyama, Cyclodextrin Chemistry, Springer, Berlin, 1978; (b) J. Szejtli, Cyclodextrins and their Inclusion Complexes, Akadémiai Kiadó, Budapest, 1982.
3. M. T. Reetz and S. R. Waldvogel, Angew. Chem., Int. Ed. Engl., 1997, 36, 865.
4. A. V. Eliseev and H. J. Schneider, J. Am. Chem. Soc., 1994, 116, 6081.
5. L. A. Godínez, J. Lin, M. Muñoz, A. W. Coleman and A. E. Kaifer, Electroanalysis, 1996, 8, 1072.
6. A. Harada, J. Li and M. Kamachi, Nature, 1993, 364, 516.
7. M. T. Rojas, R. Königer, J. F. Stoddart and A. E. Kaifer, J. Am. Chem. Soc., 1995, 117, 336; C. Henke, C. Steinem, A. Janshoff, G. Steffan, H. Luftmann, M. Sieber and H. J. Galla, Anal. Chem., 1996, 68, 3158.
8. R. Corradini, A. Dossena, G. Galaverna, R. Marchelli, A. Panagia and G. Sartor, J. Org. Chem., 1997, 62, 6283.
9. H. Asanuma, M. Kakazu, M. Shibata, T. Hishiya and M. Komiyama, Chem. Commun., 1997, 1971.
10. J. Suh, S. S. Hah and S. H. Lee, Bioorg. Chem., 1997, 25, 63.
11. R. Castro, I. Cusdrado, B. Alonso, C. M. Casado, M. Morán and A. E. Kaifer, J. Am. Chem. Soc., 1997, 119, 5760.
12. G. R. Newkome, B. D. Woosley, E. He, C. N. Moorefield, R. Güther, G. R. Baker, J. Merrill, G. H. Escamilla and H. Luftmann, Chem. Commun., 1996, 2737.
13. F. Zeng and S. C. Zimmerman, Chem. Rev., 1997, 97, 1681.
14. G. R. Newkome, C. D. Weis, C. N. Moorefield and F. R. Fronczek, Tetrahedron Lett., 1997, 38, 7053; G. R. Newkome and C. D. Weis, US Pat., 5,703,271 (Dec. 30, 1997).
15. G. R. Newkome, C. D. Weis, C. N. Moorefield, G. R. Baker, B. J. Childs and J. Epperson, Angew. Chem., Int. Ed. Engl., 1998, 37, 307; Angew. Chem., 1998, 110, 318.
16. Syntheses of the peraminated CD derivative 3 was accomplished via the following procedure: J. Boger, R. J. Corcoran and J.-M. Lehn, Helv. Chim. Acta, 1978, 61, 2190.
17. G. R. Newkome and C. D. Weis, Org. Prep. Proced. Int., 1996, 28, 485.
18. Á. Buvári and L. Barcza, J. Chem. Soc., Perkin Trans. 2, 1988, 1687.
19. (HCO₃^–/CO₃^2–I= 0.6). Prepared according to CRC Handbook of Chemistry and Physics, 72nd edn., ed. D. R. Lide, CRC Press, Boca Raton, 1991.
20. L. A. Godínez, L. Schwartz, C. M. Criss and A. E. Kaifer, J. Phys. Chem. B, 1997, 101, 3376.