Molecular design at the calamitic/discotic cross-over point. Mononuclear ortho-metallated mesogens based on the combination of rod-like phenylpyrimidines and -pyridines with bent or half-disc-shaped diketonates

Journal of Materials Chemistry

Volumn 13, Issue 5, 2003, Pages 991-1003

  Hegmann, Torsten ^a,b   Kain, Jens ^a   Diele, Siegmar ^a   Schubert, Bernd ^a   Bögel, Horst ^a   Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

^b QUEEN S UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DIFFERENTIAL SCANNING CALORIMETRY; LIGHT POLARIZATION; LIQUID CRYSTALS; SYNTHESIS (CHEMICAL); X RAY SCATTERING;

HETEROAROMATIC LIQUID CRYSTALS;

MATERIALS SCIENCE;

HETEROCYCLIC COMPOUND; KETONE DERIVATIVE; LIGAND; METAL DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE;

ARTICLE; CROSSING OVER; CRYSTALLIZATION; DIFFERENTIAL SCANNING CALORIMETRY; MICROSCOPY; MOLECULAR INTERACTION; PHASE TRANSITION; RADIATION SCATTERING; SYNTHESIS;

EID: 0037619084     PISSN: 09599428     EISSN: None     Source Type: Journal    
DOI: 10.1039/b210250a     Document Type: Article

References (70)

1. (a) J. L. Serrano, Metallomesogens, VCH, Weinheim, 1996;
2. (b) B. Donnio and D. W. Bruce, in Structure and Bonding 95: Liquid Crystals II, ed. D. M. P. Mingos, Springer, Berlin, 1999, p. 193.
3. C. Tschierske, J. Mater. Chem., 2001, 11, 2647.
4. A. C. Cope and R. W. Siekmann, J. Am. Chem. Soc., 1965, 87, 3272.
5. P. S. Pregosin, F. Wombacher, A. Albinati and F. J. Lianza, J. Organomet. Chem., 1991, 418, 249.
6. (a) M. Ghedini and D. Pucci, J. Organomet. Chem., 1990, 395, 105;
7. (b) M. Ghedini, D. Pucci, G. de Munno, D. Viterbo, F. Neve and S. Armentano, Chem. Mater., 1991, 3, 65;
8. (c) M. Ghedini, D. Pucci, E. Cesarotti, O. Francescangeli and R. Bartolino, Liq. Cryst., 1993, 15, 331.
9. (a) J. Barberá, P. Espinet, E. Lalinde, M. Marcos and J. L. Serrano, Liq. Cryst., 1987, 2, 833;
10. (b) P. Espinet, J. Etxebarria, M. Marcos, J. Pérez, A. Remón and J. L. Serrano, Angew. Chem., Int. Ed. Engl., 1989, 28, 1065;
11. (c) P. Espinet, E. Lalinde, M. Marcos, J. Pérez and J. L. Serrano, Organometallics, 1990, 9, 555;
12. (d) P. Espinet, J. Pérez, M. Marcos, M. B. Ros, J. L. Serrano, J. Barberá and A. M. Levelut, Organometallics, 1990, 9, 2028;
13. (e) M. B. Ros, N. Ruiz, J. L. Serrano and P. Espinet, Liq. Cryst., 1991, 9, 77;
14. (f) M. J. Baena, P. Espinet, M. B. Ros and J. L. Serrano, Angew. Chem., Int. Ed. Engl., 1991, 30, 711;
15. (g) M. J. Baena, P. Espinet, M. B. Ros, J. L. Serrano and A. Ezcurra, Angew. Chem., Int. Ed. Engl., 1993, 32, 1203;
16. (h) N. J. Thompson, R. Iglesias, J. L. Serrano, M. J. Baena and P. Espinet, J. Mater. Chem., 1996, 6, 1741.
17. (a) K. Praefcke, D. Singer and B. Gündogan, Mol. Cryst. Liq. Cryst., 1992, 223, 181;
18. (b) K. Praefcke, D. Singer, B. Gündogan, K. Gutbier and M. Langner, Ber. Bunsen-Ges. Phys. Chem., 1993, 97, 1358;
19. (c) K. Praefcke, D. Singer, B. Gündogan, K. Gutbier and M. Langner, Ber. Bunsen-Ges. Phys. Chem., 1993, 98, 118;
20. (d) K. Praefcke, B. Bilgin, J. Pickardt and M. Borowski, Chem. Ber., 1994, 127, 1543;
21. (e) N. Usol'tseva, K. Praefcke, D. Singer and B. Gündogan, Liq. Cryst., 1994, 16, 601;
22. (f) K. Praefcke, S. Diele, J. Pickardt, B. Gündogan, U. Nütz and D. Singer, Liq. Cryst., 1995, 18, 857;
23. (g) K. Praefcke, B. Bilgin, N. Usol'tseva, B. Heinrich and D. Guillon, J. Mater. Chem., 1995, 5, 2257;
24. (h) B. Heinrich, K. Praefcke and D. Guillon, J. Mater. Chem., 1997, 7, 1363;
25. (i) B. Bilgin Eran, D. Singer and K. Praefcke, Eur. J. Inorg. Chem., 2001, 111.
26. M. Ghedini and D. Pucci, J. Organomet. Chem., 1990, 395, 105.
27. N. J. Thompson, J. L. Serrano, M. J. Baena and P. Espinet, Chem. Eur. J., 1996, 2, 214.
28. J. Buey and P. Espinet, J. Organomet. Chem., 1996, 507, 137.
29. M. Ghedini, S. Morrone, F. Neve and D. Pucci, Gazz. Chim. Ital., 1996, 126, 511.
30. J. Buey, L. Diez, P. Espinet, H.-S. Kitzerow and J. A. Miguel, Chem. Mater., 1996, 8, 2375.
31. J. Ortega, C. L. Folcia, J. Etxebarria, M. B. Ros and J. A. Miguel, Liq. Cryst., 1997, 23, 285.
32. T. Hegmann, F. Peidis, S. Diele and C. Tschierske, Liq. Cryst., 2000, 27, 1261.
33. T. Hegmann, B. Neumann, J. Kain, S. Diele and C. Tschierske, J. Mater. Chem., 2000, 10, 2244.
34. (a) H. Zaschke, J. Prakt. Chem., 1975, 317, 617;
35. (b) G. Pelzl, P. Kolbe, U. Preukschas, D. Diele and D. Demus, Mol. Cryst. Liq. Cryst., 1979, 53, 167.
36. (a) G. Kraus and H. Zaschke, J. Prakt. Chem., 1981, 323, 199;
37. (b) A. Wiegeleben, L. Richter, J. Deresch and D. Demus, Mol. Cryst. Liq. Cryst., 1980, 59, 329;
38. (c) A. Biering, D. Demus, L. Richter, H. Sackmann and A. Wiegeleben, Mol. Cryst. Liq. Cryst., 1980, 62, 1.
39. (a) N. Mayaura, K. Yamada and A. Suzuki, Tetrahedron Lett., 1979, 3437;
40. (b) N. Mayaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
41. K. J. Edgar and S. N. Falling, J. Org. Chem., 1990, 55, 5287.
42. D. J. Mabott, B. E. Mann and P. M. Maitlis, J. Chem. Soc., Dalton Trans., 1977, 294.
43. W. Weissflog, L. Kovalenko, I. Wirth, S. Diele, G. Pelzl, H. Schmalfuss and H. Kresse, Liq. Cryst., 2000, 27, 677.
44. J. P. F. Lagerwall, F. Giesselmann and M. C. Radcliffe, Phys. Rev. E, 2002, 66, 31703.
45. Y. P. Panarin, V. Panov, O. Kalinovskaya and J. K. Vij, J. Mater. Chem., 1999, 9, 2967.
46. (a) J. S. Miller and A. J. Epstein, Prog. Inorg. Chem., 1976, 20, 1;
47. (b) J. M. Williams, Inorg. Radiochem., 1983, 26, 235;
48. (e) P. Pyykkö, Chem. Rev., 1997, 97, 597.
49. (a) J. Barbera, C. Cativiela, J. L. Serrano and J. L. Zurbano, Adv. Mater., 1991, 3, 602;
50. (b) H. Zheng, C. K. Lai and T. M. Swager, Chem. Mater., 1994, 6, 101;
51. (c) H. Zheng, B. Xu and T. M. Swager, Chem. Mater., 1996, 8, 907;
52. (d) C. K. Lai, Y. S. Pang and C. H. Tsai, J. Mater. Chem., 1998, 8, 2605;
53. (e) S. Coco, P. Espinet, J. M. Martin-Alvarez and A. M. Levelut, J. Mater. Chem., 1997, 7, 19.
54. T. A. Halgren, J. Comput. Chem., 1996, 17, 490.
55. V. Barone, L. Commisso, F. Lelj and N. Russe, Tetrahedron, 1985, 41, 1915.
56. N. Kaltsoyannis, J. Chem. Soc., Dalton Trans., 1997, 1.
57. T. Hegmann, C. Damm, G. Israel and C. Tschierske, Chem. Mater., submitted.
58. H.-T. Nguyen, C. Destrade and J. Malthête, in Handbook of Liquid Crystals, ed. D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess and V. Vill, Wiley-VCH, Weinheim, 1998, vol. 2B, p. 866.
59. P. Göring and S. Diele, in Handbook of Liquid Crystals, ed. D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess and V. Vill, Wiley-VCH, Weinheim, 1998, vol. 2B, p. 887.
60. (a) C. Tschierske, J. Mater. Chem., 1998, 8, 1485;
61. (b) K. Borisch, S. Diele, P. Göring, H. Kresse and C. Tschierske, J. Mater. Chem., 1998, 8, 529.
62. J. M. Seddon and R. H. Templer, in Handbook of Biological Physics, ed. R. Lipowsky, and E. Sackmann, Elsevier, Amsterdam, 1995, vol. 1, p. 97.
63. I. W. Hamley, The Physics of Block Copolymers, Oxford University Press, Oxford, 1998, p. 24.
64. U. Pietrasik, J. Szydlowska, A. Krowczynski, D. Pociecha, E. Gorecka and D. Guillon, J. Am. Chem. Soc., 2002, 124, 8884.
65. T. Hegmann, J. Kain, S. Diele, G. Pelzl and C. Tschierske, Angew. Chem., Int. Ed., 2001, 40, 887.
66. J. Barberá, C. Cativiela, J. L. Serrano and M. M. Zurbano, Adv. Mater., 1991, 3, 602.
67. (a) S. N. Poelsma, A. H. Servante, F. P. Fanizzi and P. M. Maitlis, Liq. Cryst., 1994, 4, 675;
68. (b) K. Ohta, H. Ema, H. Muroki, I. Yamamoto and K. Matsuzaki, Mol. Cryst. Liq. Cryst., 1987, 147, 61;
69. (c) J. Barberá, C. Cativiela, J. L. Serrano and M. M. Zurbano, Liq. Cryst., 1992, 11, 887.
70. H. Zheng, C. K. Lai and T. M. Swager, Chem. Mater., 1995, 7, 2067.