Abstract
The bisparaquat(l,4)cyclophane O4+, which can be synthesized in two steps from bipyridine and para-xylylene dibromide, is soluble as its tetrakis(hexafluorophosphate) in organic solvents such as acetonitrile and as its tetrachloride in water. In acetonitrile, O4+·4PF6− forms weak 1:1 inclusion complexes with 1,2−, 1,3−, and 1,4-dimethoxybenzene whereas, in water, 04+·4Cl− binds hydroquinol as well as its dimethyl ether. X-Ray crystallography shows that the bisparaquat(1,4)cyclophane tetracation O4+ forms crystalline 1:1 inclusion complexes with 1,2− and 1,4-dimethoxybenzenes in which the π-electron rich diphenol ethers are sited inside the channels of the π-electron deficient bipyridinium rings of the tetracation O4+ separated, as before, by layers of anions and neutral molecules in continuous hollow stacks of a zeolitic nature.
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References
Colquhoun, H. M.; Stoddart, J. F.; Williams, D. J. New Scientist 1986,1 May, 44.
Allwood, B. L.; Spencer, N.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1064.
Stoddart, J. F. Pure Appl. Chem. 1988, 60, 467.
Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1070.
Ito, M. M.; Kato, J.; Takagi, S.; Nakashiro, E.; Sato, T.; Yamada, Y.; Saito, H.; Namiki, T.; Takamura, L; Wakatsuki, K.; Suzuki, T.; Endo, T. J. Am. Chem. Soc. 1988,110, 5147.
Beevers, C. A. Proceedings of the European Crystallographic Meeting; Zurich, 1976; 293; Cheney, B. V.; Schulz, M. W.; Cheney, J.; Richards, W. G. Am. Chem. Soc. 1988,110, 4195.
Moody, G. J.; Owusu, R. K.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Thomas, J. D. R.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1987, 26, 890; Alston, D. R.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J.; Zarzycki, R. Angew. Chem., Int. Ed. Engl. 1987, 26, 692, 693.
Gould, R. O.; Gray. A. M.; Taylor, P.; Walkinshaw, M. D. Am. Chem. Soc. 1985,107, 5921; Burley, S. K.; Petsko, G. A. J. Am. Chem. Soc. 1986,108, 7995.
Ashton, P. R.; Chrystal, E. J. T.; Mathias, J. P.; Parry, K. P.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Tetrahedron Lett. 1987, 28, 6367.
Ortholand, J.-Y.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., in press.
Geuder, W.; Hünig, S.; Suchy, A. Angew. Chem.t Int. Ed. Engl. 1983, 22, 489; Tetrahedron 1986, 42, 1665; Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1988,27, 1547.
Muller, W. M.; Vögtle, F. Angew. Chem., Int. Ed. Engl 1984, 23, 712; Franke, J.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1985, 24, 219.
Ashton, P. R.; Odell, B.; Reddington, M. V.; Slawin, A. M. Z.; Stoddart, J. F.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1550; see also Buhner, M.; Geuder, W.; Gries, W.-K.; Hünig, S.; Koch, M.; Poll, T. Angew. Chem., Int. Ed. Engl. 1988,27, 1553.
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© 1990 Plenum Press, New York
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Reddington, M.V., Spencer, N., Stoddart, J.F. (1990). Complexation and Molecular Recognition of Neutral and Anionic Substrates in the Solid and Solution States by Bisparaquat(1,4)Cyclophane. In: Atwood, J.L. (eds) Inclusion Phenomena and Molecular Recognition. Springer, Boston, MA. https://doi.org/10.1007/978-1-4613-0603-0_4
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DOI: https://doi.org/10.1007/978-1-4613-0603-0_4
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