Skip to main content
Log in

Quantitative self-assembly of a [2]catenane from two preformed molecular rings

  • Letter
  • Published:

From Nature

View current issue Submit your manuscript

Abstract

MOLECULES composed of interlocking rings are termed catenanes. Since the first synthesis of a two-ring catenane (a [2]catenane) in 19601, these and related interlinked compounds have attracted considerable interest2–10, in part from the perspective of forming molecular devices and nanoscale architectures11,12. Here we report the formation of a [2]catenane from two complete rings, reminiscent of the trick of interlinking 'magic rings'. This supermolecule, 1 in Fig. 1, exists in rapid equilibrium with the monomeric rings 2, as revealed by 1H NMR and electrospray mass spectrometry. At low concentration of molecule 2, the equilibrium lies towards the monomers, but at higher concentrations the catenane is the overwhelmingly dominant species in solution.

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. Wasserman, E. J. Am. chem. Soc. 82, 4433–4434 (1960).

    Article  CAS  Google Scholar 

  2. Dietrich-Buchecker, C. O. & Sauvage, J.-P. Chem. Rev. 87, 795–810 (1987).

    Article  CAS  Google Scholar 

  3. Ashton, P. R. et al. Angew. Chem. int. Edn engl. 28, 1396–1399 (1989).

    Article  Google Scholar 

  4. Ashton, P. R. et al. Angew. Chem. int. Edn engl. 30, 1039–1042 (1991).

    Article  Google Scholar 

  5. Ashton, P. R. et al. Angew. Chem. int. Edn engl. 30, 1042–1044 (1991).

    Article  Google Scholar 

  6. Anelli, P. L. et al. J. Am. chem. Soc. 114, 193–218 (1992).

    Article  CAS  Google Scholar 

  7. Hunter, C. A. J. Am. chem. Soc. 114, 5303–5311 (1992).

    Article  CAS  Google Scholar 

  8. Vögtle, F., Meier, S. & Hoss, R. Angew. Chem. int. Edn engl. 31, 1619–1622 (1992).

    Article  Google Scholar 

  9. Ogino, H. J. Am. chem. Soc. 103, 1303–1304 (1981).

    Article  CAS  Google Scholar 

  10. Harada, A., Li, J. & Kamachi, M. Nature 356, 325–327 (1992).

    Article  ADS  CAS  Google Scholar 

  11. Anelli, P. L., Spencer, N. & Stoddart, J. F. J. Am. chem. Soc. 113, 5131–5133 (1991).

    Article  CAS  Google Scholar 

  12. Molecular Electronic Devices (eds Carter, F. L. & Siatowski, R. E.) (North-Holland, Amsterdam, 1988).

  13. Fujita, M., Nagao, S., Iida, M., Ogata, K. & Ogura, K. J. Am. chem. Soc. 115, 1574–1576 (1993).

    Article  CAS  Google Scholar 

  14. Fujita, M., Yazaki, J. & Ogura, K. Chem. Lett. 1031–1032 (1991).

    Article  Google Scholar 

  15. Fujita, M., Yazaki, J. & Ogura, K. J. Am. chem. Soc. 112, 5645–5647 (1990).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fujita, M., Ibukuro, F., Hagihara, H. et al. Quantitative self-assembly of a [2]catenane from two preformed molecular rings. Nature 367, 720–723 (1994). https://doi.org/10.1038/367720a0

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1038/367720a0

  • Springer Nature Limited

This article is cited by

Navigation