Skip to main content
Log in

Crystalline inclusion compounds derived from bulky organosilicon hosts – design, synthesis, structure and stability

  • Published:
Silicon Chemistry

Abstract

New organosilicon compounds 13 featuring bulky triphenylsilyl moieties attached to rigid linear or trigonal spacer units have been synthesized and demonstrated to act as clathrate hosts, yielding crystalline inclusion compounds mostly with apolar and aprotic dipolar guest molecules, while the nonbulky dimethylphenylsilyl or trimethylsilyl substituted analogous compounds 4 and 5, which were also synthesized, proved inefficient. X-ray crystal structures of the inclusion compounds 1·DMF (1:1), 1·pyridine (1:1), 2·1,4-dioxane (2:1), 2·pyridine (2:1), 2·p-xylene (2:1), 2·H2O (2:1) as well as of the unsolvated compounds 2 and 5 are described, and thermal stability studies of selected clathrates are reported.

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. Weber, E. 1995 In Kirk-Othmer Encyclopedia of Chemical Technology, 4th Ed., Vol. 14, ed. J. I. Kroschwitz, pp. 122-154. New York: Wiley.

    Google Scholar 

  2. Atwood, J.L. Davies, J.E.D. & MacNicol, D.D., eds. 1991 Inclusion Compounds, Vols. 4 and 5. Oxford, UK: Oxford University Press.

    Google Scholar 

  3. Steed, W.J. & Atwood, J.L. 2000 Supramolecular Chemistry. Chichester, UK: Wiley.

    Google Scholar 

  4. Weber, E. & Czugler, M. 1988. In Molecular Inclusion and Molecular Recognition--Clathrates II, Topics in Current Chemistry, Vol. 149, ed. E. Weber, pp. 45-135. Berlin-Heidelberg: Springer-Verlag.

    Google Scholar 

  5. Bishop, R. 1996 Chem. Soc. Rev. 311.

  6. Aoyama, Y. 1998 In Design of Organic Solids, Topics in Current Chemistry, Vol. 198, ed. E. Weber, pp. 131-161. Berlin-Heidelberg: Springer-Verlag.

    Google Scholar 

  7. MacNicol, D.D. Toda, F. & Bishop, R. eds. 1996 Comprehensive Supramolecular Chemistry, Vol. 6. Oxford, UK: Elsevier.

    Google Scholar 

  8. More recent examples: (a) Weber, E., Nitsche, S., Wierig, A. & Csöregh, I. 2002 Eur. J. Org. Chem. 856. (b) Toda, F., Hirano, S., Toyota, S., Kato, M., Sugio, Y. & Hachiya, T. 2002 Cryst. Eng. Commun. 4, 171.

  9. Dastidar, P. & Goldberg, I. 1996. In Comprehensive Supramolecular Chemistry Vol. 6, eds. D.D. MacNicol, F. Toda & R. Bishop, p. 305. Oxford, UK: Elsevier.

    Google Scholar 

  10. Not to consider the so-called ‘coordination polymers’ which do not involve individual host molecules. Molecular Self Assembly-Organic Versus Inorganic Approaches, Structure and Bonding, Vol. 96, ed. M. Fujita. Berlin-Heidelberg: Springer-Verlag, 2000.

  11. Bourne, S.A., Johnson, L., Marais, C., Nassimbeni, L.R., Weber, E., Skobridis, K. & Toda, F. 1991 J. Chem. Soc., Perkin Trans. 2, 1707.

    Google Scholar 

  12. Bourne, S.A., Nassimbeni, L.R., Skobridis, K. & Weber, E. 1991 J. Chem. Soc., Chem. Commun. 282.

  13. Weber, E., Skobridis, K., Wierig, A. & Goldberg, I. 1997 J. Incl. Phenom. 28, 163.

    Google Scholar 

  14. Weber, E., Skobridis, K. & Goldberg, I. 1989 J. Chem. Soc., Chem. Commun. 1195.

  15. Desiraju, G.R. 1996. In Comprehensive Supramolecular Chemistry Vol. 6, eds. D.D. MacNicol, F. Toda & R. Bishop, p. 1. Oxford, UK: Elsevier.

    Google Scholar 

  16. Müller, T., Hulliger, J., Seichter, W., Weber, E., Weber, T. & Wübbenhorst, M. 2000 Chem. Eur. J. 6, 54.

    Google Scholar 

  17. Weber, E., Hecker, M., Koepp, E., Orlia, W., Czugler, M. & Csöregh, I. 1988 J. Chem. Soc., Perkin Trans. 2, 1251.

    Google Scholar 

  18. Nitsche, S., Weber, E., Trommer, K. & Roewer, G. 2000. In Organosilicon Chemistry IV -- From Molecules to Materials, eds. N. Auner & J. Weis, pp. 312-316. Weinheim: Wiley-VCH.

    Google Scholar 

  19. Takahashi, S., Kuroyama, Y., Sonogashira, K. & Hagihara, N. 1980 Synthesis 627.

  20. Ciana, L.D. & Haim, A. 1984 J. Heterocycl. Chem. 21, 607.

    Google Scholar 

  21. Weber, E., Hens, T., Li, Q. & Mak, C.W. 1999 Eur. J. Org. Chem. 1115.

  22. Nishio, M., Hirota, M. & Umezawa, Y. 1998 The CH/πInteraction--Evidence, Nature and Consequences. New York: Wiley-VCH.

    Google Scholar 

  23. Desiraju, G.R. & Steiner, T. 1999 The Weak Hydrogen Bond, IUCr Monographs on Crystallography. Oxford, UK: Oxford University Press.

    Google Scholar 

  24. Lide, D.R. & Kehiaian, H.V. eds. 1994 CRC Handbook of Thermophysical and Thermochemical Data. Boca Raton, FL: CRC Press.

    Google Scholar 

  25. Patai, S. & Rappoport, Z. eds. 1989 The Chemistry of Organic Silicon Compounds New York: Wiley.

    Google Scholar 

  26. (a) Reinbold, J., Cammann, K., Weber, E., Hens, T. & Reutel, C. 1999 J. Prakt. Chem. 341, 252. (b) Dickert, F. L. & Haunschild, A. 1993 Adv. Mater. 5, 887.

    Google Scholar 

  27. (a) Reinhoudt, D.N. ed. 1996 Comprehensive Supramolecular Chemistry, Vol. 10. Oxford, UK: Elsevier; (b) Atwood, L., Davies, J.E.D. & MacNicol, D.D. eds. 1984 Inclusion Com-pounds, Vol. 3. London: Academic Press.

    Google Scholar 

  28. Melissaris, A.P. & Litt, M.H. 1992 J. Org. Chem. 57, 6998.

    Google Scholar 

  29. McBride, J.A.H. & Wade, K. 1996 Synth. Commun. 26, 2309.

    Google Scholar 

  30. Sheldrick, G.M. 1986 SHELXS-93: Program for Crystal Structure Solution. Germany: University of Göttingen.

    Google Scholar 

  31. Sheldrick, G.M. 1993 SHELXL-93: Program for Refinement of Crystal Structures. Germany: University of Göttingen.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nitsche, S.I., Weber, E., Seichter, W. et al. Crystalline inclusion compounds derived from bulky organosilicon hosts – design, synthesis, structure and stability. Silicon Chemistry 2, 55–71 (2003). https://doi.org/10.1023/B:SILC.0000047934.01345.7d

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:SILC.0000047934.01345.7d

Navigation