Abstract
The evolution of lariat ethers from relatively simple, substituted crown ethers into electrochemically sensitive ligands is presented. Although nitrogen-pivot lariats were observed to be better binders than the corresponding parent crowns and to retain considerable flexibility after complexation, overall stability constants were not favorable for cation transport applications. This led to the syntheses of nitrobenzene- and anthraquinone-substituted systems capable of reversible redox behavior and drastically enhanced cation binding abilities when reduced. Application of these in enhanced cation transport processes has been demonstrated.
Similar content being viewed by others
References
C. J. Pedersen:J. Am. Chem. Soc. 87, 7017 (1967).
J.-M. Lehn:Science 227, 849 (1985).
D. J. Cram and K. Trueblood: ‘Concept, Structure and Binding in Complexation’, in F. Vögtle and E. Weber (Eds.)Host-Guest Complex Chemistry: Macrocycles, Springer Verlag, 1985, 125–188.
G. W. Liesegang and E. M. Eyring: ‘Kinetic Studies of Synthetic Multidentate Macrocyclic Ligands’, inSynthetic Multidentate Macrocyclic Compounds, R. M. Izatt and J. J. Christensen, Eds.; Academic Press, New York, 1978, p. 245.
G. W. Gokel, D. M. Dishong, and C. J. Diamond:J. Chem. Soc., Chem. Commun. 1053 (1980); (b) D. M. Dishong, C. J. Diamond, and G. W. Gokel:Tetrahedron Lett. 1663 (1981); (c) R. A. Schultz, D. M. Dishong, and G. W. Gokel:Tetrahedron Lett. 2623 (1981); (d) R. A. Schultz, D. M. Dishong, and G. W. Gokel:J. Am. Chem. Soc. 104, 625 (1982); (c) R. A. Schultz, E. Schlegel, D. M. Dishong, and G. W. Gokel:J. Chem. Soc., Chem. Commun. 242 (1982); (f) Y. Nakatsuji, T. Nakamura, M. Okahara, D. M. Dishong, and G. W. Gokel:Tetrahedron Lett. 1351 (1982).
A. Kaifer, H. D. Durst, L. Echegoyen, D. M. Dishong, R. A. Schultz, and G. W. Gokel:J. Org. Chem. 47, 3195 (1982); (b) H. D. Durst, L. Echegoyen, G. W. Gokel, and A. Kaifer:Tetrahedron Lett. 4449 (1982); (b) L. Echegoyen, A. Kaifer, H. D. Durst, and G. W. Gokel:J. Org. Chem. 49, 688 (1984); (c) A. Kaifer, L. Echegoyen, H. Durst, R. A. Schultz, D. M. Dishong, D. M. Goli, G. W. Gokel:J. Am. Chem. Soc. 106, 5100 (1984).
A. Kaifer, L. Echegoyen, D. Gustowski, D. M. Goli, and G. W. Gokel:J. Am. Chem. Soc. 105, 7168 (1983); (b) D. A. Gustowski, L. Echegoyen, D. M. Goli, A. Kaifer, R. A. Schultz, and G. W. Gokel,J. Am. Chem. Soc. 106, 1633 (1984).
D. M. Dishong, C. J. Diamond, M. I. Cinoman, and G. W. Gokel:J. Am. Chem. Soc. 105, 586 (1983).
R. A. Schultz, B. D. White, D. M. Dishong, K. A. Arnold, and G. W. Gokel:J. Am. Chem. Soc. 107, 6659 (1985).
G. W. Gokel, D. M. Goli, C. Minganti, and L. Echegoyen:J. Am. Chem. Soc. 105, 6786 (1985).
B. G. Cox, H. Schneider, J. Stroka:J. Am. Chem. Soc. 100, 4746 (1978); (b) M.-F. Lejaille, M.-H. Livertoux, C. Guidon, and J. Bessiere:Bull. Soc. Chim. Fr. 1373 (1978); (c) B. G. Cox, J. Garcia-Rosas, and H. Schneider;J. Am. Chem. Soc. 103, 1384 (1981).
F. R. Fronczek, V. J. Gatto, R. A. Schultz, S. J. Jungk, W. J. Colucci, R. D. Gandour, and G. W. Gokel:J. Am. Chem. Soc. 105, 6717 (1983); (b) F. R. Fronczek, V. J. Gatto, C. Minganti, R. A. Schultz, R. D. Gandour, and G. W. Gokel:J. Am. Chem. Soc. 106, 7244 (1984); (c) B. D. White, K. A. Arnold, F. R. Fronczek, R. D. Gandour, and G. W. Gokel:Tetrahedron Lett. 26,4035 (1985); (d) R. D. Gandour, F. R. Fronczek, V. J. Gatto, C. Minganti, R. A. Schultz, B. D. White, K. A. Arnold, D. Mazzocchi, S. R. Miller, and G. W. Gokel:J. Am. Chem. Soc. 108, 4078 (1986).
(a) L. Echegoyen, G. W. Gokel, M. S. Kin, E. M. Eyring, and S. Petrucci:J. Phys. Chem. 3854 (1987); (b) G. W. Gokel, L. Echegoyen, M. S. Kim, E. M. Eyring, and S. Petrucci:Biophys. Chem. 26, 225 (1987).
A. Kaifer, D. A. Gustowski, L. Echegoyen, V. J. Gatto, R. A. Schultz, T. P. Cleary, C. R. Morgan, A. M. Rios, and G. W. Gokel:J. Am. Chem. Soc. 107, 1958 (1985).
D. A. Gustowski, V. J. Gatto, A. Kaifer, L. Echegoyen, R. E. Godt, and G. W. Gokel:J. Chem. Soc., Chem. Commun. 923 (1984).
L. Echegoyen, D. A. Gustowski, V. J. Gatto, and G. W. Gokel:J. Chem. Soc., Chem. Commun. 220 (1986).
M. Delgado, L. Echegoyen, V. J. Gatto, Vincent, D. A. Gustowski, and G. W. Gokel:J. Am. Chem. Soc. 108, 4135 (1986); (b) D. A. Gustowski, M. Delgado, V. J. Gatto, L. Echegoyen, and G. W. Gokel:Tetrahedron Lett. 3487 (1986); (c) D. A. Gustowski, M. Delgado, V. J. Gatto, L. Echegoyen, and G. W. Gokel:J. Am. Chem. Soc. 108, 7553 (1986).
M. Delgado, D. A. Gustowski, H. K. Yoo, V. J. Gatto, G. W. Gokel, and L. Echegoyen:J. Am. Chem. Soc. 110, 119 (1988).
L. Echeverria, M. Delgado, V. J. Gatto, G. W. Gokel and L. Echegoyen:J. Am. Chem. Soc. 108, 6825 (1986).
T. Saji:J. Chem. Soc., Chem. Commun. 716 (1986).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Echegoyen, L., Gokel, G.W., Echegoyen, L.E. et al. Electrochemical switching in reducible lariat ethers: From cation binding enhancements to electrochemically-mediated transport. J Incl Phenom Macrocycl Chem 7, 257–266 (1989). https://doi.org/10.1007/BF01060726
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01060726