Synthesis and physical properties of novel guanidine containing molecular clips. Strong host-guest binding and formation of a lyotropic liquid crystalline phase

Chemical Communications

Volumn , Issue 2, 1996, Pages 241-243

  Gieling, Gerben T W ^a   Scheeren, Hans W ^a   Israël, Randy ^a   Nolte, Roeland J M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842419455     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000241     Document Type: Article

References (14)

1. For an overview of the complexation of neutral guest molecules by different hosts see: R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261; R. Liu and W. C. Still, Tetrahedron Lett., 1993, 34, 2573; M. M. Conn, G. Deslongchamps, J. de Mendoza and J. Rebek, J. Am. Chem. Soc., 1993, 115, 3548; B. J. Whitlock and H. W. Whitlock, J. Am. Chem. Soc., 1994, 116, 2301.
2. For an overview of the complexation of neutral guest molecules by different hosts see: R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261; R. Liu and W. C. Still, Tetrahedron Lett., 1993, 34, 2573; M. M. Conn, G. Deslongchamps, J. de Mendoza and J. Rebek, J. Am. Chem. Soc., 1993, 115, 3548; B. J. Whitlock and H. W. Whitlock, J. Am. Chem. Soc., 1994, 116, 2301.
3. For an overview of the complexation of neutral guest molecules by different hosts see: R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261; R. Liu and W. C. Still, Tetrahedron Lett., 1993, 34, 2573; M. M. Conn, G. Deslongchamps, J. de Mendoza and J. Rebek, J. Am. Chem. Soc., 1993, 115, 3548; B. J. Whitlock and H. W. Whitlock, J. Am. Chem. Soc., 1994, 116, 2301.
4. For an overview of the complexation of neutral guest molecules by different hosts see: R. M. Izatt, J. S. Bradshaw, K. Pawlak, R. L. Bruening and B. J. Tarbet, Chem. Rev., 1992, 92, 1261; R. Liu and W. C. Still, Tetrahedron Lett., 1993, 34, 2573; M. M. Conn, G. Deslongchamps, J. de Mendoza and J. Rebek, J. Am. Chem. Soc., 1993, 115, 3548; B. J. Whitlock and H. W. Whitlock, J. Am. Chem. Soc., 1994, 116, 2301.
5. (a) R. P. Sijbesma and R. J. M. Nolte, J. Org. Chem., 1991, 56, 3122;
6. (b) R. P. Sijbesma, A. P. M. Kentgens and R. J. M. Nolte, J. Org. Chem., 1991, 56, 3199;
7. (c) R. P. Sijbesma, A. P. M. Kentgens, E. T. G. Lutz, J. H. van der Maas and R. J. M. Nolte, J. Am. Chem. Soc., 1993, 115, 8999.
8. Y. Yamamoto and S. Kojima, in The Chemistry of Amidines and Imidates, ed. S. Patai and Z. Rappoport, Wiley-Interscience, Chichester, 1991, vol. 2, p. 505.
9. In other papers we have described the aggregation behaviour of aza-crown ether modified clips: J. L. M. van Nunen, R. S. A. Stevens, S. J. Picken and R. J. M. Nolte, J. Am. Chem. Soc., 1994, 116, 8825; A. P. H. J. Schenning, B. de Bruin, M. C. Feiters and R. J. M. Nolte, Angew. Chem., 1994, 106, 1741; Angew. Chem., Int. Ed. Engl., 1994, 33, 1662.
10. In other papers we have described the aggregation behaviour of aza-crown ether modified clips: J. L. M. van Nunen, R. S. A. Stevens, S. J. Picken and R. J. M. Nolte, J. Am. Chem. Soc., 1994, 116, 8825; A. P. H. J. Schenning, B. de Bruin, M. C. Feiters and R. J. M. Nolte, Angew. Chem., 1994, 106, 1741; Angew. Chem., Int. Ed. Engl., 1994, 33, 1662.
11. In other papers we have described the aggregation behaviour of aza-crown ether modified clips: J. L. M. van Nunen, R. S. A. Stevens, S. J. Picken and R. J. M. Nolte, J. Am. Chem. Soc., 1994, 116, 8825; A. P. H. J. Schenning, B. de Bruin, M. C. Feiters and R. J. M. Nolte, Angew. Chem., 1994, 106, 1741; Angew. Chem., Int. Ed. Engl., 1994, 33, 1662.
12. R. P. Sijbesma and R. J. M. Nolte, Red. Trav. Chim. Pays-Bas, 1993, 112, 643.
13. R. Israël, K. L. Beurskens, G. T. W. Gieling, R.J. M. Nolte, J. M. M. Smits, P. T. Beurskens, manuscript in preparation.
14. Self-association was recently found to occur in many of our clip molecules. A. E. Rowan, J. N. H. Reek and R. J. M. Nolte, unpublished results.