Skip to main content
SpringerLink
Log in

Inclusions between large flat organic molecules; the induction of columns and mesophases

  • Review Article
  • Published:
Journal of inclusion phenomena and molecular recognition in chemistry Aims and scope Submit manuscript

Abstract

We describe here an overview on the formation of mesophases by the interaction between large flat aromatic cored molecules and relatively small organic electron acceptors which form stacked, sandwich-like columnar π-π electron donor-acceptor complexes. The inclusion of suitable donor and acceptor components may be used to induce columnar mesophases in mixtures of compounds which can be either mesomorphic or non-mesomorphic in the pure state. With judicious choice of donor and acceptor partners, induced mesophases of remarkable range and thermal stability can be prepared.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Part 96 on liquid crystalline compounds. Part 95: N. Utsol'tseva, G. Hauck, H.D. Koswig, K. Praefcke, and B. Heinrich:Liq. Cryst. 20, 731 (1996).

    Google Scholar 

  2. F. Reinitzer:Monatsh. Chemie 9, 421 (1888); reprinted and translated in English:Liq. Cryst. 5, 7(1989).

    Google Scholar 

  3. M. J. S. Dewar:An Introduction to Modern Chemistry, Oxford Univ. Press (1965).

  4. G. W. Gray, K. J. Harrison, and J. A. Nash:Electron. Lett. 9, 130 (1973).

    Google Scholar 

  5. C. Hilsum:The anatomy of a discovery— biphenyl liquid crystals (in Technology of Chemicals and Materials for Electronics, Ed. E. R. Howells), chapter 3, pp. 43–58, Ellis Horwood (1984).

  6. P.-G. de Gennes:Angew. Chem. 104, 856 (1992);Angew. Chem. Int. Ed. Engl. 31, 842 (1992).

    Google Scholar 

  7. J.-M. Lehn:Angew. Chem. 100, 91 (1988);Angew. Chem. Int. Ed. Engl. 27, 89 (1988).

    Google Scholar 

  8. C. Destrade, M. C. Mondon, and J. Malthête:J. Phys. 40, C3 (1979).

    Google Scholar 

  9. W. Kreuder, and H. Ringsdorf:Makromol. Chem., Rapid Commun. 4, 807 (1983).

    Google Scholar 

  10. N. Boden, R. J. Bushby, L. Ferris, C. Hardy, and F. Sixl:Liq. Cryst. 1, 109 (1986).

    Google Scholar 

  11. B. Kohne, W. Poules, and K. Praefcke:Chem.-Ztg. 108, 113 (1984).

    Google Scholar 

  12. B. Kohne, K. Praefcke, T. Derz, V. Frischmuth, and C. Gansau:Chem.-Ztg. 108, 408 (1984).

    Google Scholar 

  13. B. Kohne, and K. Praefcke:Chimia 41, 196 (1987).

    Google Scholar 

  14. K. Praefcke, B. Kohne, K. Gutbier, N. Johnen, and D. Singer:Liq. Cryst. 5, 233 (1989).

    Google Scholar 

  15. K. Praefcke, B. Kohne, and D. Singer:Angew. Chem 102, 200 (1990);Angew. Chem. Int. Ed. Engl. 29, 177 (1990).

    Google Scholar 

  16. K. Praefcke, B. Kohne, D. Singer, D. Demus, G. Pelzl, and S. Diele:Liq. Cryst. 7, 589 (1990).

    Google Scholar 

  17. G. A. Jeffrey, and L. M. Wingert:Liq. Cryst. 12, 179 (1992).

    Google Scholar 

  18. K. Praefcke, D. Blunk, and J. Hempel:Mol. Cryst. Liq. Cryst. 243, 323 (1994).

    Google Scholar 

  19. H. Prade, R. Miethchen, and V. Vill:J. Prakt. Chem. 337, 427 (1995).

    Google Scholar 

  20. K. Praefcke, and D. Singer:Mol. Mater. 3, 265 (1994).

    Google Scholar 

  21. G. Pelzl, D. Demus, and H. Sackmann:Z. Phys. Chem. 238, 22 (1968).

    Google Scholar 

  22. N. K. Sharma, G. Pelzl, D. Demus, and Weissflog:Z Phys. Chem. 238, 22 (1968).

    Google Scholar 

  23. W. H. De Jeu, L. Longa, and D. Demus:J. Chem. Phys. 84, 293 (1986).

    Google Scholar 

  24. M. Ebert, G. Frick, C. Baehr, J. H. Wendorff, R. Wüstefeld, and H. Ringsdorf:Liq. Cryst. 11, 293 (1992).

    Google Scholar 

  25. J. S. Dave, and R. A. Vora:Influence of Molecular Structure and Composition on the Liquid Crystals formed by Mixtures of Nonamphiphilic Compounds (in Liquid Crystals & Plastic Crystals v. 1, Eds. G. W Gray and P A. Winsor), Chapter 4.2, pp. 153–174, Ellis Horwood (1974).

  26. N. D. Revannasiddaiah, and D. Krishnamurti:Mol. Cryst. Liq. Cryst. 101, 103 (1983).

    Google Scholar 

  27. B. Engelen, G. Heppke, R. Hopf, and F. Schneider:Ann. Phys. 3, 403 (1978).

    Google Scholar 

  28. M. Domon, and J. Billard:J. Phys., Paris C40, C3 (1979).

    Google Scholar 

  29. P. E. Cladis:Mol. Cryst. Liq. Cryst. 67, 177 (1981).

    Google Scholar 

  30. D. Demus, G. Pelzl, N. K. Sharma, and W. Weissflog:Mol. Cryst. Liq. Cryst. 76, 241 (1981).

    Google Scholar 

  31. C. R. Patrick, and G. S. Prosser:Nature 187, 1021 (1960).

    Google Scholar 

  32. P. Davison, A.-M. Levelut, H. Strzelecka, and V. Gionis:J. Phys. Lett. 44, L-823 (1983).

    Google Scholar 

  33. V. Gionis, H. Strzelecka, M. Veber, R. Kormann, and L. Zuppiroli:Mol. Cryst. Liq. Cryst. 137, 365 (1986).

    Google Scholar 

  34. L. J. Andrews:Chem. Rev. 54, 713 (1954).

    Google Scholar 

  35. H. Ringsdorf, R. Wüstefeld, E. Zerta, M. Ebert, and J. H. Wendorff.Angew. Chem. 101, 934 (1989);Angew. Chem. Int. Ed. Engl. 28, 914 (1989).

    Google Scholar 

  36. H. Bengs, O. Karthaus, H. Ringsdorf, C. Baehr, M. Ebert, and J. H. Wendorff:Liq. Cryst. 10, 161 (1991).

    Google Scholar 

  37. H. Bengs, M. Ebert, O. Karthaus, B. Kohne, K. Praefcke, H. Ringsdorf, J. H. Wendorff, and R. Wüstefeld:Adv. Mater 2, 141 (1990).

    Google Scholar 

  38. K. Praefcke, D. Singer, B. Kohne, M. Ebert, A. Liebmann, and J. H. Wendorff:Liq. Cryst. 10, 147 (1991).

    Google Scholar 

  39. M. Ebert, D. A. Jungbauer, R. Kleppinger, J. H. Wendorff, B. Kohne, and K. Praefcke:Liq. Cryst. 4, 53 (1989).

    Google Scholar 

  40. K. Praefcke, D. Singer, M. Langner, B. Kohne, M. Ebert, A. Liebmann, and J. H. Wendorff:Mol. Cryst. Liq. Cryst. 215, 121 (1992).

    Google Scholar 

  41. K. Praefcke, D. Singer, and A. Eckert:Liq. Cryst. 16, 53 (1994).

    Google Scholar 

  42. B. Sabaschus, D. Singer, G. Heppke, and K. Praefcke:Liq. Cryst. 12, 863 (1992).

    Google Scholar 

  43. D. Janietz, K. Praefcke, and D. Singer:Liq. Cryst. 13, 247 (1993).

    Google Scholar 

  44. K. Praefcke, D. Singer, and B. Kohne:Liq. Cryst. 13, 445 (1993).

    Google Scholar 

  45. J. Malthête, C. Destrade, H. T. Nguyen, and J. Jacques:Mol. Cryst. Liq. Cryst. 64, 233 (1981).

    Google Scholar 

  46. C. Destrade, H. T. Nguyen, J. Malthête, and J. Jacques:Phys. Lett. A 79, 189 (1980).

    Google Scholar 

  47. K. Praefeke, D. Singer, and B. Gündogan:Mol. Cryst. Liq. Cryst. 223, 181 (1992).

    Google Scholar 

  48. B. Gündogan, and K. Praefeke:Chem. Ber. 126, 1253 (1993).

    Google Scholar 

  49. D. Singer, A. Liebmann, K. Praefcke, and J. H. Wendorff:Liq. Cryst. 14, 785 (1993).

    Google Scholar 

  50. N. Usol'tseva, K. Praefcke, D. Singer, and B. Gündogan:Liq. Cryst. 16, 601 (1994); see also reference [1].

    Google Scholar 

  51. N. Usol'tseva, K. Praefcke, D. Singer, and B. Gündogan:Liq. Cryst. 16, 617 (1994).

    Google Scholar 

  52. N. Usol'tseva, K. Praefcke, D. Singer, and B. Gündogan:Mol. Mater. 4, 253 (1994).

    Google Scholar 

  53. K. Praefcke, B. Bilgin, J. Pickardt, and M. Borowski:Chem. Ber. 127, 1543 (1994).

    Google Scholar 

  54. K. Praefcke, S. Diele, J. Pickardt, B. Gündogan, U. Nütz, and D. Singer:Liq. Cryst. 18, 857 (1995).

    Google Scholar 

  55. K. Praefcke, B. Bilgin, N. Usol'tseva, B. Heinrich, and D. Guillon:J. Mater. Chem. 5, 2257 (1995).

    Google Scholar 

  56. J. M. Vila, M. Gayoso, T. Pereira, C. Rodriguez, J. M. Ortigueira, and M. Thornton-Pelt:J. Organomet. Chem. 426, 267 (1992).

    Google Scholar 

  57. J. Barbera, P. Espinet, E. Lalinde, M. Marcos, and J. L. Serrano:Liq. Cryst. 2, 833 (1987).

    Google Scholar 

  58. T. K. Attwood, J. E. Lydon, C. Hall, and G. J. T. Tiddy:Liq. Cryst. 7, 657 (1990); and an earlier paper cited therein.

    Google Scholar 

  59. A. Liebmann, C. Mertesdorf, T. Plesnivy, H. Ringsdorf, and J. H. Wendorff:Angew. Chem. 103, 1358 (1991);Angew. Chem. Int. Ed. Engl. 30, 1375 (1991).

    Google Scholar 

  60. G. Lattermann, S. Schmidt, R. Kleppinger, and J. H. Wendorff.Adv. Mater. 4, 30 (1992).

    Google Scholar 

  61. M. Möller, V. Tsukruk, J. H. Wendorff, H. Bengs, and H. Ringsdorf.Liq. Cryst. 12, 17 (1992). Remark added in proof (May 22, 1996): other examples by a relatively long flexible spacer covalently linked donor-acceptor mesogens are based on our disc-like radial multiynes [e.g., 13, 14, 38, 40, 43] as just published: D. Janietz,J. Chem. Soc., Chem. Commun. 713 (1996).

    Google Scholar 

  62. P. Henderson, S. Kumar, J. A. Rego, H. Ringsdorf, and P Schubmacher:J. Chem. Soc., Chem. Commun. 1059 (1995).

  63. N. Boden, R. J. Bushby, and A. N. Cammidge:Liq. Cryst. 18, 673 (1995).

    Google Scholar 

  64. K. Praefcke, A. Eckert, and D. Blunk: unpublished results. Our transition temperatures of1h, k, and1, presented in Figure 10 were determined by DSC (Mettler TA 3000/DSC-30 S with TA 72.5 software) given to the nearest degree, °C; cf. those of1h [63] Cr <25 °C D h (Col h ) 136 °C Iso. NMR (1H and13C) and MS spectra prove the molecular structures of these three liquid crystals; in each case, their purity is ≽99.4 mol-% (DSC).

  65. N. Boden, R. J. Bushby, A. N. Cammidge, and G. Headdock:J. Mater. Chem. 5, 2275 (1995).

    Google Scholar 

  66. K. Praefcke, D. Singer, B. Gündogan, K. Gutbier, and M. Langner:Ber. Bunsenges. Phys. Chem. 97, 1358 (1993). For other nitrile or trifluoromethyl substituted radial multiynes (here pentaynes) see reference [40].

    Google Scholar 

  67. K.P. is grateful to Mrs. Dr. E. A. Corsellis, Strasbourg, France, who, in connection with our discussion, brought as another example the following papers to our attention: D. Guillon, P. Weber, A. Skoulios, C. Piechocki, and J. Simon:Mol. Cryst. Liq. Cryst. 130, 223 (1985), and C. Piechocki, and J. Simon:J. Chem. Soc., Chem. Commun. 1985, 259.

    Google Scholar 

  68. D. Adam, P. Schuhmacher, J. Simmerer, L. Haussling, K. Siemensmeyer, K. H. Etzbach, H. Ringsdorf, and D. Haarer:Nature 371, 141 (1994); see also a commentary inChem. Eng. News. 72, 19 (1994).

    Google Scholar 

  69. N. Boden, R. J. Bushby, and J. Clements:J. Chem. Phys. 98, 5920 (1993); and papers cited therein.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institut für Organische Chemie, Technische Universität Berlin, Straße des 17 Juni 135, D-10623, Berlin, Germany

    Klaus Praefcke & John D. Holbrey

Authors
  1. Klaus Praefcke
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. John D. Holbrey
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See Ref. [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Praefcke, K., Holbrey, J.D. Inclusions between large flat organic molecules; the induction of columns and mesophases. J Incl Phenom Macrocycl Chem 24, 19–41 (1996). https://doi.org/10.1007/BF01053424

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01053424

Key words

Search

Navigation