The importance of micro segregation for mesophase formation: Thermotropic columnar mesophases of tetrahedral and other low-aspect-ratio organic materials

Chemistry - A European Journal

Volumn 5, Issue 5, 1999, Pages 1643-1660

  Pegenau, Annegret ^a   Hegmann, Torsten ^a   Tschierske, Carsten ^a   Diele, Siegmar ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Block molecules; Liquid crystals; Micro segregation; Non covalent interactions; Supramolecular chemistry

Indexed keywords

AMINOALCOHOL; BENZENE DERIVATIVE; ORGANIC COMPOUND; PENTAERYTHRITOL; TETRAHEDRAL PENTAERYTHRITOL DERIVATIVE; TETRAHEDRAL ZINC BIS(1,3 DIKETONATE); TETRAPHENYLMETHANE DERIVATIVE; TETRAPHENYLSTANNANE; TOLUENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; DIFFERENTIAL SCANNING CALORIMETRY; LIQUID CRYSTAL; POLARIZATION MICROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION;

EID: 0032915751     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990503)5:5<1643::AID-CHEM1643>3.0.CO;2-T     Document Type: Article

References (81)

1. Handbook of Liquid Crystals, Vol. 1-3 (Eds.: D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, V. Vill), Wiley-VCH, Weinheim, 1998.
2. a) H. Fischer, S. S. Ghosh, P. A. Heiny, N. C. Maliszewskyj, T. Plesnivy, H. Ringsdorf, M. Seitz, Angew. Chem. 1995, 107, 879; Angew. Chem. Int. Ed. Engl. 1995, 34, 795;
3. a) H. Fischer, S. S. Ghosh, P. A. Heiny, N. C. Maliszewskyj, T. Plesnivy, H. Ringsdorf, M. Seitz, Angew. Chem. 1995, 107, 879; Angew. Chem. Int. Ed. Engl. 1995, 34, 795;
4. b) M. Seitz, T. Plesnivy, K. Schimossek, M. Edelmann, H. Ringsdorf, H. Fischer, H. Uyama, S. Kobayashi, Macromolecules 1996, 29, 6560.
5. a) U. Stebani, G. Lattermann, M. Wittenberg, R. Festtag, J. H. Wendorff, Adv. Mater. 1994, 6, 572;
6. b) U. Stebani, G. Lattermann, Adv. Mater. 1995, 7, 578;
7. c) U. Stebani, G. Lattermann, Macromol. Rep. 1995, A32 (Suppl. 3) 385;
8. d) U. Stebani, G. Lattermann, M. Wittenberg, J. H. Wendorff, J. Mater. Chem. 1997, 7, 607.
9. J. H. Cameron, A. Facher, G. Lattermann, S. Diele, Adv. Mater. 1997, 9, 398.
10. V. S. K. Balagurusamy, G. Ungar, V. Percec, G. Johansson, J. Am. Chem. Soc. 1997, 119, 1539.
11. a) A.-M. Giroud-Godquin, A. Rassat, C. R. Acad. Sci. 1982, 294, 241;
12. b) H. Zheng, T. M. Swager, J. Am. Chem. Soc. 1994, 111, 761;
13. c) T. M. Swager, H. Zheng, Mol. Cryst. Liq. Cryst. 1995, 260, 301.
14. J. Malthete, A. M. Levelut, Adv. Mater. 1991, 3, 94.
15. Preliminary reports: a) A. Pegenau, P. Göring, C. Tschierske, Proceedings of the 25. Freiburger Arbeitstagung Flüssigkristalle, Freiburg, 1996, P55;
16. b) A. Pegenau, P. Göring, C. Tschierske, Chem. Commun. 1996, 2563;
17. c) A. Pegenau, P. Göring, S. Diele, C. Tschierske, SPIE 1998, 3319, 70.
18. a) J. Charvolin, J. Chim. Phys. 1983, 80, 15;
19. b) A. Skoulios, D. Guillon, Mol. Cryst. Liq. Cryst. 1988, 165, 317;
20. c) Y. Hendrikx, A. M. Levelut, Mol. Cryst. Liq. Cryst. 1988, 165, 233.
21. C. Tschierske, H. Zaschke, J. Prakt. Chem. 1989, 331, 365.
22. C. Tschierske, H. Kresse, H. Zaschke, D. Demus, Mol. Cryst. Liq. Cryst. 1990, 188, 1.
23. T. J. Dunn, W. L. Neumann, M. M. Rogic, S. R. Woulfe, J. Org. Chem. 1990, 55, 6368.
24. K. Praefcke, P. Psaras, A. Eckert, Liq. Cryst. 1993, 13, 551.
25. Organikum, 15th ed., VEB, Berlin, 1984, p. 614.
26. A. Roedig, in Methoden der Organischen Chemie (Hauben Weyl) Vol V/4 (Ed.: E. Müller), 4th ed., Thieme, Stuttgart, 1960, p. 390.
27. Organikum, 15th ed., VEB, Berlin, 1984, p. 490.
28. C. F. Nutaitis, G. W. Gribble, Org. Prepr. Proced. Int. 1985, 17, 11.
29. a) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981, II, 513;
30. b) M. Hird, G. W. Gray, K. J. Toyne, Mol. Cryst. Liq. Cryst. 1991, 206, 187.
31. C. M. Wilson, A. C. Griffin, J. Mater. Chem. 1993, 3, 991.
32. C. Sauer, S. Diele, N. Lindner, C. Tschierske, Liq. Cryst. 1998, 25, 109.
33. H. Gilmann, L. A. Gist, J. Org. Chem. 1957, 22, 368.
34. K. Ohta, H. Ema, H. Muroki, I. Yamamoto, K. Matsuzaki, Mol. Cryst. Liq. Cryst. 1987, 147, 61.
35. A. N. Cammidge, R. J. Bushby, in Handbook of Liquid Crystals, Vol. 2B (Eds.: D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, V. Vill), Wiley-VCH, Weinheim, 1998, 693.
36. a) A. Eckert, B. Kohne, K. Praefcke, Z. Naturforsch B 1988, 43, 878;
37. b) K. Praefcke, B. Kohne, A. Eckert, J. Hempel, Z. Naturforsch. B 1990, 45, 1084;
38. c) K. Praefcke, P. Marquardt, B. Kohne, W. Stephan, J. Carbohydr. Chem. 1991, 10, 539;
39. d) G. Lattermann, G. Staufer, Liq. Cryst. 1989, 4, 347;
40. e) V. Percee, J. Heck, G. Johansson, D. Tomazos, M. Kawasumi, G. Ungar, J. Macromol. Sci. Pure Appl. Chem. 1994, A31, 1031;
41. f) V. Percee, G. Johannson, J. Heck, G. Ungar, S. V. Batty, J. Chem. Soc. Perkin Trans. 1 1993, 1411.
42. a) K. Borisch, S. Diele, P. Göring, C. Tschierske, Chem. Commun. 1996, 237;
43. b) K. Borisch, S. Diele, P. Göring, H. Müller, C. Tschierske, Liq. Cryst. 1997, 22, 427;
44. c) K. Borisch, S. Diele, P. Göring, H. Kresse, C. Tschierske, J. Mater. Chem. 1998, 8, 529.
45. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
46. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
47. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
48. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
49. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
50. There are several other classes of compounds in which columnar mesophases have been found, for example, rectangular, oblique and sometimes also hexagonal columnar thermomesophases can be found in polycatenar molecules (J. Malthete, H. T. Nguyen, C. Destrade, Liq. Cryst. 1993, 13, 171.), in anhydrous soaps (A. Skoulios, V. Luzzati, Acta Crystallogr. 1961, 14, 278), in rod-coil molecules (M. Lee, N.-K. Oh, W.-C. Zin, Chem. Commun. 1996, 1787), in calamitic molecules with lateral polar groups (F. Hildebrandt, J. A. Schröter, C. Tschierske, R. Festag, M. Wittenberg, J. H. Wendorff, Adv. Mater, 1997, 9, 564), and rectangular and oblique columnar phases were found as modulated smectic phases of polar calamitic compounds (F. Hardouin, A. M. Levelut, M. F. Achart, G. Sigaud, J. Chim. Phys. 1983, 80, 53). Also rodlike polymers, such as polyglutamates can form columnar mesophases (R. Sakamoto, A. Osawa, Mol. Cryst. Liq. Cryst. 1987, 153, 385).
51. C. Tschierske, J. Mater. Chem. 1998, 8, 1485.
52. a) A. E. Skoulios, in Developments in Block Copolymers, Vol. 1 (Ed.: I. Goldman) Applied Science, 1982, p. 81;
53. b) A. Skoulios, in Advances in Liquid Crystals, (Ed.: G. H. Brown), Academic Press, New York, 1975, p. 169;
54. c) A. Skoulios, D. Guillon, Mol. Cryst. Liq. Cryst. 1988, 165, 317;
55. d) F. S. Bates, G. H. Fredrickson, Annu. Rev. Phys. Chem. 1990, 41, 525.
56. L. Leibler, Macromolecules 1980, 13, 1602.
57. a) D. J. Meier, Block Copolymers: Science and Technology, IMM/Harwood Academic, New York, 1983;
58. b) D. J. Meier, J. Polym. Sci. C 1969, 26, 81.
59. D. W. Van Krevelen, Properties of Polymers, 3rd ed., Elsevier, Amsterdam, 1990, p. 189.
60. a) J. M. Lehn, J. Malthete, A. M. Levelut, J. Chem. Soc. Chem. Commun. 1985, 1794;
61. b) G. Lattermann, Mol. Cryst. Liq. Cryst. 1990, 182B, 299;
62. c) G. Lattermann, Liq. Cryst. 1989, 6, 619;
63. d) C. Mertensdorf, H. Ringsdorf, Liq. Cryst. 1989, 5, 1757;
64. e) S. H. J. Idziak, N. C. Maliszewskyj, P. A. Heiney, J. P. McCauley, Jr., P. A. Sprengeler, A. B. Smith, III, J. Am. Chem. Soc. 1991, 113, 7666;
65. f) S. H. J. Idziak, N. C. Maliszewskyj, G. B. M. Vaughan, P. A. Heiney, C. Mertensdorf, H. Ringsdorf, J. P. McCauley, Jr., A. B. Smith, III, J. Chem. Soc. Chem. Commun. 1992, 98;
66. g) J. Malthete, D. Poupinet, R. Vilanove, J. M. Lehn, J. Chem. Soc. Chem. Commun. 1989, 1016;
67. h) M. Zhao, W. T. Ford, S. H. J. Idziak, N. C. Maliszewsky, P. A. Heiney, Liq. Cryst. 1994, 4, 583.
68. Pentaerythritol was also used as the central liking unit to obtain oligomeric calamitic liquid crystals: a) R. Eidenschink, F. H. Kreutzer, W. H. De Jeu, Liq. Cryst. 1990, 8, 879;
69. b) K. Zab, O. Agert, D. Joachimi, B. Neumann, C. Tschierske, Liq. Cryst. 1995, 18, 489;
70. c) K. Zab, D. Joachimi, E. Novotna, S. Diele, C. Tschierske, Liq. Cryst. 1995, 18, 489;
71. d) J. Andersch, S. Diele, D. Lose, C. Tschierske, Liq. Cryst. 1996, 21, 103.
72. The first tetraphenylmethane derivatives were synthesized and investigated with respect to their mesomorphic behaviour in the Vorländer group: H. Voigt, PhD thesis, Universität Halle, 1924. These Schiff-base derivatives with terminal methoxy groups have no liquid-crystalline properties.
73. Starlike rigid multipodes consisting of an adamantane core and rigid oligophenylenes arms were synthesized with the aim to induce molecular reinforcement effects in mixtures with polymer matrices: B. Schartel, V. Stümpflen, J. Wending, J. H. Wendorff, W. Heitz, R. Neuhaus, Colloid Polym. Sci. 1996, 274, 919.
74. [6] It seems that additional interactions between the metal centers could be responsible for mesophase formation in the octahedral metallomesogens.
75. G. Staufer, Dissertation, Bayreuth 1990, 47.
76. Likewise, the columnar mesophases of alkanoylated chito-oligosacharides become less stable and less ordered on increasing the degree of oligomerization: M. Sugiura, M. Minoda, J. Watanabe, T. Miyamoto, Polym. J. 1994, 26, 1236.
77. J. Malthete, A. Collet, A. M. Levelut, Liq. Cryst. 1989, 5, 123.
78. J. Malthete, New. J. Chem. 1996, 20, 925.
79. C. Destrade, H. T. Nguyen, C. Alstermark, G. Lindsten, M. Nillson, B. Otterholm, Mol. Cryst. Liq. Cryst. 1990, 180, 265.
80. J. W. Goodby, M. Hird, K. J. Toyne, T. Watson, J. Chem. Soc. Chem. Commun. 1994, 1701.
81. D. R. Coulson, L. C. Satek, S. O. Grim, Inorg. Synth. 1973, 13, 121.