Skip to main content
Log in

Synthesis and properties of biphenyl-containing fluorenonophanes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A novel family of crownophanes containing 2,7-dioxyfluorenone and 4,4′-dioxybiphenyl fragments linked by tri- and tetraethylene glycol residues was obtained. The formation of pseudorotaxanes in reactions of these ligands with paraquat hexafluorophosphate was detected by FAB mass spectrometry, 1H NMR spectroscopy, and electronic absorption spectroscopy.

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. J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives, Wiley-VCH, Weinheim, 1995.

    Google Scholar 

  2. J. W. Steed, J. L. Atwood, Supramolecular Chemistry, Wiley, New York, 2000.

    Google Scholar 

  3. D. J. Cram, J. M. Cram, Container Molecules and Their Guests, The Royal Society of Chemistry, Cambridge, 1994.

    Google Scholar 

  4. F. Diederich, Cyclophanes, The Royal Society of Chemistry, Cambridge, 1991.

    Google Scholar 

  5. K. Müller-Dethlefs, P. Hobza, Chem. Rev., 2000, 100, 143.

    Article  Google Scholar 

  6. L. M. Grieg, D. Philp, Chem. Soc. Rev., 2001, 30, 287.

    Article  Google Scholar 

  7. S. J. Cantrill, D. A. Fulton, A. M. Heiss, A. R. Pease, J. F. Stoddart, A. J. P. White, D. J. Williams, Chem. Eur. J., 2000, 6, 2274.

    Article  CAS  Google Scholar 

  8. M. S. Cubberley, B. L. Iverson, J. Am. Chem. Soc., 2001, 123, 7560.

    Article  CAS  Google Scholar 

  9. S. R. Seidel, P. J. Stang, Acc. Chem. Res., 2002, 35, 972.

    Article  CAS  Google Scholar 

  10. R. Vilar, Angew. Chem., Int. Ed., 2003, 42, 1460.

    Article  CAS  Google Scholar 

  11. T. J. Hubin, D. H. Busch, Coord. Chem. Rev., 2000, 200–202, 5.

    Article  Google Scholar 

  12. J. F. Stoddart, H.-R. Tseng, Proc. Natl. Acad. Sci. USA, 2002, 99, 4797.

    Article  CAS  Google Scholar 

  13. H.-J. Schneider, A. Yatsimirski, Principles and Methods in Supramolecular Chemistry, Wiley, Chichester, 2000.

    Google Scholar 

  14. H.-R. Tseng, S. A. Vignon, P. C. Celestre, J. Perkins, J. O. Jeppesen, A. Di Fabio, R. Ballardini, M. T. Gandolfi, M. Venturi, V. Balzani, J. F. Stoddart, Chem. Eur. J., 2004, 10, 155.

    Article  CAS  Google Scholar 

  15. D. B. Amabilino, J. F. Stoddart, Chem. Rev., 1995, 95, 2725.

    Article  CAS  Google Scholar 

  16. Molecular Catenanes, Rotaxanes and Knots, Eds J.-P. Sauvage and C. O. Dietrich-Buchecker, Wiley-VCH, Weinheim, 1999.

    Google Scholar 

  17. D. B. Amabilino, J. F. Stoddart, Chem. Rev., 1995, 95, 2725.

    Article  CAS  Google Scholar 

  18. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart, Angew. Chem., Int. Ed., 2000, 39, 3348.

    Article  CAS  Google Scholar 

  19. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines — A Journey into the Nano World, Wiley-VCH, Weinheim, 2003.

    Book  Google Scholar 

  20. J. W. Choi, A. H. Flood, D. W. Steuerman, S. Nygaard, A. B. Braunschweig, N. N. P. Moonen, B. W. Laursen, Y. Luo, E. DeIonno, A. J. Peters, J. O. Jeppesen, K. Xu, J. F. Stoddart, J. R. Heath, Chem. Eur. J., 2006, 12, 261.

    Article  CAS  Google Scholar 

  21. V. Balzani, A. Credi, B. Ferrer, S. Silvi, M. Venturi, Top. Curr. Chem., 2005, 262, 1.

    Article  CAS  Google Scholar 

  22. Molecular Switches, Ed. B. L. Feringa, Wiley-VCH, Weinheim, 2001.

    Google Scholar 

  23. J. Liu, M. Gómez-Kaifer, A. E. Kaifer, in Molecular Machines and Motors, Ed. J.-P. Sauvage, Struct. Bonding, 2001, 99, 141.

  24. N. G. Luk’yanenko, A. Yu. Lyapunov, T. I. Kirichenko, Izv. Akad. Nauk, Ser. Khim., 2007, 951 [Russ. Chem. Bull., Int. Ed., 2007, 56, 986].

    Google Scholar 

  25. J. D. Badjic, S. J. Cantrill, J. F. Stoddart, J. Am. Chem. Soc., 2004, 126, 2288.

    Article  CAS  Google Scholar 

  26. B. Long, K. Nikitin, D. Fitzmaurice, J. Am. Chem. Soc., 2003, 125, 15490.

    Article  CAS  Google Scholar 

  27. F. Huang, K. A. Switek, L. N. Zakharov, F. R. Fronczek, C. Slebodnick, M. Lam, J. A. Golen, W. S. Bryant, P. E. Mason, A. L. Rheingold, M. Ashraf-Khorassani, H. W. Gibson, J. Org. Chem., 2005, 70, 3231.

    Article  CAS  Google Scholar 

  28. A. Credi, S. Dumas, S. Silvi, M. Venturi, A. Arduini, A. Pochini, A. Secchi, J. Org. Chem., 2004, 69, 5881.

    Article  CAS  Google Scholar 

  29. M. Kwangyul, A. E. Kaifer, Org. Lett., 2004, 6, 185.

    Article  Google Scholar 

  30. M. Vincenti, J. Mass Spectrom., 1995, 30, 925.

    Article  CAS  Google Scholar 

  31. C. A. Schalley, Int. J. Mass Spectrom., 2000, 194, 11.

    Article  CAS  Google Scholar 

  32. E. J. Mahan, J. A. Dennis, Org. Lett., 2006, 8, 5085.

    Article  CAS  Google Scholar 

  33. M. Asakawa, P. R. Ashton, W. Dehaen, G. L’abbe, S. Menzer, J. Nouwen, F. M. Raymo, J. F. Stoddart, M. S. Tolley, S. Toppet, A. J. P. White, D. J. Williams, Chem. Eur. J., 1997, 3, 772.

    Article  CAS  Google Scholar 

  34. N. G. Lukyanenko, A. Yu. Lyapunov, T. I. Kirichenko, R. I. Zubatyuk, O. V. Shishkin, Mendeleev Commun., 2006, 16, 143.

    Article  Google Scholar 

  35. P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spenser, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc., 1992, 114, 193.

    Article  CAS  Google Scholar 

  36. M. Asakawa, P. R. Ashton, V. Balzani, S. E. Boyd, A. Credi, G. Mattersteig, S. Menzer, M. Montalti, F. M. Raymo, C. Ruffilli, J. F. Stoddart, M. Venturi, D. J. Williams, Eur. J. Org. Chem., 1999, 985.

  37. R. Ballardini, V. Balzani, A. Di Fabio, M. T. Gandolfi, J. Becher, J. Lau, M. B. Nielsen, J. F. Stoddart, New J. Chem., 2001, 25, 293.

    Article  CAS  Google Scholar 

  38. Spartan’ 06, Wavefunction, Inc. Irvine, CA.

  39. E. A. Meyer, R. K. Castellano, F. Diederich, Angew. Chem., Int. Ed., 2003, 42, 1210.

    Article  CAS  Google Scholar 

  40. W. B. Jennings, B. M. Farrell, J. F. Malone, Acc. Chem. Res., 2001, 34, 885.

    Article  CAS  Google Scholar 

  41. C. A. Hunter, K. R. Lawson, J. Perkins, C. J. Urch, J. Chem. Soc., Perkin Trans. 2, 2001, 651.

  42. K. N. Houk, S. Menzer, S. P. Newton, F. M. Raymo, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc., 1999, 121, 1479.

    Article  CAS  Google Scholar 

  43. N. A. Barnes, R. W. Faessinger, J. Org. Chem., 1961, 26, 4544.

    Article  CAS  Google Scholar 

  44. A. Manjula, M. Nagarajan, Arkivoc, 2001, 165.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to N. G. Luk’yanenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1665–1670, May, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Luk’yanenko, N.G., Kirichenko, T.I., Lyapunov, A.Y. et al. Synthesis and properties of biphenyl-containing fluorenonophanes. Russ Chem Bull 57, 1697–1702 (2008). https://doi.org/10.1007/s11172-008-0224-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0224-3

Key words

Navigation