Self-assembly of a [2 × 2] hydrogen bonded grid

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Piotr Lipkowski, Anna Bielejewska, Peter Timmerman, David N. Reinhoudt, Huub Kooijman and Anthony L. Spek


Abstract

Formation of 24 cooperative hydrogen bonds drives the spontaneous assembly of a rigid bifunctional trimelamine and bis(barbituric acid) to give selectively the [2 × 2] hydrogen-bonded grid, in preference to the corresponding [1 × 1] or polymeric assemblies.


References

  1. M.-T. Youinou, N. Rahmouni, J. Fischer and J. A. Osborn, Angew. Chem., Int. Ed. Engl., 1992, 31, 733 CrossRef.
  2. P. N. W. Baxter, J.-M. Lehn, J. Fischer and M.-T. Youinou, Angew. Chem., Int. Ed. Engl., 1994, 33, 2284 CrossRef.
  3. P. N. W. Baxter, J.-M. Lehn, B. Kneisel and D. Fenske, Chem. Commun., 1997, 2231 RSC.
  4. G. S. Hanan, D. Volkmer, U. S. Schubert, J.-M. Lehn, G. Baum and D. Fenske, Angew. Chem., Int. Ed. Engl., 1997, 36, 1842 CrossRef.
  5. J.-M. Lehn, Supramolecular Chemistry, Concepts and Perspectives, VCH, Weinheim, 1995 Search PubMed.
  6. S.-K. Chang and A. D. Hamilton, J. Am. Chem. Soc., 1988, 110, 1318 CrossRef CAS; J.-M. Lehn, M. Mascal, A. DeCian and J. Fischer, J. Chem. Soc., Chem. Commun., 1990, 479 RSC; J. P. Mathias, E. E. Simanek, J. A. Zerkowski, C. T. Seto and G. M. Whitesides, J. Am. Chem. Soc., 1994, 116, 4316 CrossRef CAS.
  7. C. M. Marjo, unpublished results.
  8. J. Yang, E. Fan, S. J. Geib and A. D. Hamilton, J. Am. Chem. Soc., 1993, 115, 5314 CrossRef CAS.
  9. J. P. Mathias, E. E. Simanek and G. M. Whitesides, J. Am. Chem. Soc., 1994, 116, 4326 CrossRef CAS.
  10. A. C. Cope, H. L. Holmes and H. O. House, Org. React., 1957, 9, 107.
  11. E. Fischer and A. Dilthey, Ann., 1904, 335, 334 Search PubMed.
  12. K. A. Jolliffe, M. Crego Calama, R. Fokkens, N. M. M. Nibbering, P. Timmerman and D. N. Reinhoudt, Angew. Chem., Int. Ed., 1998, 37, 1294 CrossRef CAS.
  13. J. Rao, J. Lahiri, L. Isaacs, R. M. Weis and G. M. Whitesides, Science, 1998, 280, 708 CrossRef CAS.
  14. M. Mammen, E. E. Simanek and G. M. Whitesides, J. Am. Chem. Soc., 1996, 118, 12614 CrossRef CAS.
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