Skip to main content
Log in

Amplification of Chirality in Helical Supramolecular Columns

  • Published:
Journal of inclusion phenomena and macrocyclic chemistry Aims and scope Submit manuscript

Abstract

Strong amplification of chirality occurs in dynamic, but highly ordered, helical columns in n-butanol, for which one chiral seed molecule suffices to render a column of 400 molecules to become homochiral. The chiral columns are formed in a thermally dependent stepwise process. The transition from achiral stacks to helical columns is highly cooperative owing to well-defined intermolecular interactions. `Sergeant and Soldiers' measurements allow for the calculation of the association constant and cooperativity length of the homochiral segments. The `Sergeant and Soldiers' data on the number of molecules within a column show a strikingly good match with data obtained from a theoretical model describing the self-assembly of the discotic molecules as a function of temperature and concentration.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. B.L. Feringa and R.A. van Delden: Angew. Chem., Int. Ed. 38, 3418 (1999).

    Google Scholar 

  2. M. Avalos, R. Babiano, P. Cintas, J. L. Jiménez, and J.C. Palacios: Chem. Commun. 887 (2000).

  3. M. Farina: The stereochemistry of linear macromolecules, in E.L. Eliel and S.H. Wilen (eds.), Topics in Stereochemistry, Iss17, pp. 1-112, John Wiley & Sons, New York (1987).

    Google Scholar 

  4. M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, and S. Lifson: Science 268, 1860 (1995).

    Google Scholar 

  5. M.M. Green, M.P. Reidy, R.J. Johnson, G. Darling, D.J. O'Leary, and G. Wilson: J. Am. Chem. Soc. 111, 6454 (1989).

    Google Scholar 

  6. A.R.A. Palmans, J.A.J.M. Vekemans, E.E. Havinga, and E.W. Meijer: Angew. Chem., Int. Ed. Engl. 36, 2648 (1997).

    Google Scholar 

  7. L. Brunsveld, A.P.H.J. Schenning, M.A.C. Broeren, H.M. Janssen, J.A.J.M. Vekemans, and E.W. Meijer: Chem. Lett. 292 (2000).

  8. B.M.W. Langeveld-Voss, R.J.M. Waterval, R.A.J. Janssen, and E.W. Meijer: Macromolecules 32, 227 (1999).

    Google Scholar 

  9. R.K. Castellano, C. Nuckolls, and J. Rebek Jr.: J. Am. Chem. Soc. 121, 11156 (1999).

    Google Scholar 

  10. L.J. Prins, J. Huskens, F. de Jong, P. Timmerman, and D.N. Reinhoudt: Nature 398, 498 (1999).

    Google Scholar 

  11. J.H.K.K. Hirschberg, L. Brunsveld, A. Ramzi, J.A.J.M. Vekemans, R.P. Sijbesma, and E.W.Meijer: Nature 407, 167 (2000).

    Google Scholar 

  12. L. Brunsveld, B.G.G. Lohmeijer, J.A.J.M. Vekemans, and E.W. Meijer: Chem. Commun. 2305 (2000).

  13. L. Brunsveld, H. Zhang, M. Glasbeek, J.A.J.M. Vekemans, and E.W. Meijer: J. Am. Chem. Soc. 122, 6175 (2000).

    Google Scholar 

  14. P. van der Schoot, T. Michels, L. Brunsveld, R.P. Sijbesma, and A. Ramzi: Langmuir 16, 10076 (2000).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brunsfeld, L., Lohmeijer, B.G., Vekemans, J.A. et al. Amplification of Chirality in Helical Supramolecular Columns. Journal of Inclusion Phenomena 41, 61–64 (2001). https://doi.org/10.1023/A:1014417621324

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1014417621324

Navigation