Liquid crystalline derivatives of oligoethylene-amines and -amino ethers with amide, ester, urea or urethane functions

Abstract

The mesomorphism of diethylenetriamine and triethylenetetramine derivatives, substituted with the 3,4-bis(decyloxy)benzoyl group (‘two chain’ substituent)via amide, ester, urea or urethane moieties, is described. Furthermore, different examples of related linear and cyclic oligoethyleneamino ethers are investigated and compared with the mesomorphism of the first group. Both lamellar smectic A and hexagonal columnar mesophases can be observed in linear compounds, depending on the length of the linear unit. A cyclic derivative displays a cubic phase. The conclusion is emphasized that the mesomorphism of these classes of compounds is caused by microphase separation.

References

1. J.-M. Lehn, J. Malthête and A.-M. Levelut, J. Chem. Soc., Chem. Commun., 1985, 1794.
2. C. Mertesdorf and H. Ringsdorf, Liq. Cryst., 1989, 5, 1757.
3. G. Lattermann, Liq. Cryst., 1989, 6, 619.
4. J. Malthête, D. Poupinet, R. Vilanove and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1989, 1016.
5. G. Lattermann, Mol. Cryst. Liq. Cryst., 1990, 182B, 299.
6. D. Tatarsky, K. Banerjee and W. T. Ford, Chem. Mater., 1990, 2, 138.
7. C. Mertesdorf, H. Ringsdorf and J. Stumpe, Liq. Cryst., 1991, 9, 337.
8. S. H. J. Idziak, N. C. Maliszewskyj, P. A. Heiney, J. P. McCauley, Jr., P. A. Sprengler and A. B. Smith, III, J. Am. Chem. Soc., 1991, 113, 7666.
9. J. Malthête, A.-M. Levelut and J.-M. Lehn, J. Chem. Soc., Chem. Commun., 1992, 1434.
10. S. H. J. Idziak, N. C. Maliszewskyj, G. B. M. Vaughan, P. A. Heiney, C. Mertesdorf, H. Ringsdorf, J. P. McCauley, Jr. and A. B. Smith, III, J. Chem. Soc., Chem. Commun., 1992, 98.
11. M. Zhao, W. T. Ford, S. H. J. Idziak, N. C. Maliszweskyj and P. A. Heiney, Liq. Cryst., 1994, 16, 583.
12. H. Fischer, S. S. Ghosh, P. A. Heiney, N. C. Maliszewskyj, T. Plesnivy, H. Ringsdorf and M. Seitz, Angew. Chem., 1995, 107, 879; Angew. Chem., Int. Ed. Engl., 1995, 34, 795.
13. M. Seitz, T. Plesnivy, K. Schimossek, M. Edelmann, H. Ringsdorf, H. Fischer, H. Uyama and S. Kobayashi, Macromolecules, 1996, 29, 6560.
14. A. Liebmann, C. Mertesdorf, T. Plesnivy, H. Ringsdorf and J. H. Wendorff, Angew. Chem., 1991, 103, 1358; Angew. Chem., Int. Ed. Engl., 1991, 30, 1375.
15. U. Stebani, G. Lattermann, R. Festag, M. Wittenberg and J. H. Wendorff, Adv. Mater., 1994, 6, 572, 790.
16. U. Stebani, G. Lattermann, R. Festag, M. Wittenberg and J. H. Wendorff, J. Mater. Chem., 1995, 5, 2247.
17. U. Stebani and G. Lattermann, Macromol. Rep., 1995, A32(Suppl. 3), 385.
18. U. Stebani and G. Lattermann, Adv. Mater., 1995, 7, 578.
19. G. Lattermann, S. Schmidt and B. Gallot, J. Chem. Soc., Chem. Commun., 1992, 1091.
20. G. Lattermann, S. Schmidt, R. Kleppinger and J. H. Wendorff, Adv. Mater., 1992, 4, 30.
21. S. Schmidt, G. Lattermann, R. Kleppinger and J. H. Wendorff, Liq. Cryst., 1994, 16, 693.
22. H. Fischer, T. Plesnivy, H. Ringsdorf and M. Seitz, J. Chem. Soc., Chem. Commun., 1995, 1615.
23. U. Stebani, PhD Thesis, University of Bayreuth, 1995.
24. U. Stebani, G. Lattermann, M. Wittenberg and J. H. Wendorff, Angew. Chem., 1996, 108, 1941; Angew. Chem., Int. Ed. Engl., 1996, 35, 1858.
25. R. Festag, PhD Thesis, University of Marburg, 1995.
26. F. Neve, M. Ghedini and O. Francesangeli, Liq. Cryst., 1996, 21, 625.
27. M. Litt, F. Rahl and L. G. Roldan, J. Polym. Sci., Part A: Polym. Chem., 1969, 7, 463.
28. J. N. Israelachvili, Intermolecular and Surface Forces, Academic Press, New York, 1992, p. 380.
29. H. Hoffmann and G. Ebert, Angew. Chem., Int. Ed. Engl., 1988, 27, 902.
30. R. Stadler, C. Auschra, J. Beckmann, U. Krappe, I. Voigt-Martin and L. Leibler, Macromolecules, 1995, 28, 3080.
31. A. Skoulios and D. Guillon, Mol. Cryst. Liq. Cryst., 1988, 165, 317.
32. R. P. Tuffin, K. J. Toyne and J. W. Goodby, J. Mater. Chem., 1995, 5, 2093.
33. R. P. Tuffin, K. J. Toyne and J. W. Goodby, J. Mater. Chem., 1996, 6, 1271.
34. V. Percec, J. Heck, G. Johansson, D. Tomazos, M. Kawasumi and G. Ungar, J. Macromol. Sci.-Pure Appl. Chem., 1994, A31, 1031.
35. D. C. Sun and J. H. Magill, Polymer, 1987, 28, 1243.
36. V. S. Papkov, M. N. Il'ina, V. P. Zhukov, D. J. Tsvankin and D. R. Tur, Macromolecules, 1992, 25, 2033 and references cited therein.
37. G. J. Out, A. A. Turetskii, M. Möller and D. Oelfin, Macromolecules, 1994, 27, 3310 and references cited therein.
38. A. Turetskii, G. J. J. Out, H.-A. Klok and M. Möller, Polymer, 1995, 36, 1303.
39. V. Percec, D. Schlueter, J. C. Ronda, G. Johansson, G. Ungar and J. P. Zhou, Macromolecules, 1996, 29, 1464.
40. J. Watanabe and Y. Takashina, Macromolecules, 1991, 24, 3423.
41. P. Weber, D. Guillon, A. Skoulios and R. D. Miller, J. Phys. (Paris), 1989, 50, 793.
42. E. K. Karikari, A. J. Greso, B. L. Farmer, R. D. Miller and J. F. Rabolt, Macromolecules, 1993, 26, 3937.
43. J. Malthête, A. M. Levelut and H. T. Nguyen, J. Phys. Lett., 1985, 46, L-875.
44. K. Praefcke, B. Bilgin, N. Usolt'tseva, B. Heinrich and D. Guillon, J. Mater. Chem., 1995, 5, 2257.
45. S. Diele, D. Lose, G. Pelzl, E. Dietzmann, F. Guittard and W. Weissflog, Freiburger Arbeitstagung Flüssigkristalle, 1996, 25 abstract Nr. 09.
46. M. Schellhorn and G. Lattermann, Liq. Cryst., 1994, 17, 529.
47. Organikum, ed. H. G. O. Becker, J. A. Barth, Leipzig, 1993, p. 594f.