Oligopyridine liquid crystals - Novel building blocks for supermolecular architectures based on metal coordination and hydrogen bonding

Angewandte Chemie - International Edition

Volumn 39, Issue 14, 2000, Pages 2454-2458

  Tschierske, Carsten ^a  

^a MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

Copper; Liquid crystals; Metallomesogens; Nitrogen heterocycles; Palladium

Indexed keywords

COORDINATION COMPOUND; METAL; OLIGOPYRIDINE; PALLADIUM; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

CRYSTALLIZATION; CYTOARCHITECTURE; DERIVATIZATION; HYDROGEN BOND; LIQUID CRYSTAL; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; REVIEW;

EID: 0034679470     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20000717)39:14<2454::AID-ANIE2454>3.0.CO;2-7     Document Type: Review

References (68)

1. J. M. Lehn, Supramolecular Chemistry; Concepts and Perspectives, VCH, Weinheim, 1995; E. C. Constable, Metals and Ligand Reactivity: An Introduction to Organic Chemistry of Metal Complexes, VCH, Weinheim, 1995; F. M. Raymo, J. F. Stoddart, Curr. Opin. Colloid Interf. Sci. 1998, 3, 150.
2. J. M. Lehn, Supramolecular Chemistry; Concepts and Perspectives, VCH, Weinheim, 1995; E. C. Constable, Metals and Ligand Reactivity: An Introduction to Organic Chemistry of Metal Complexes, VCH, Weinheim, 1995; F. M. Raymo, J. F. Stoddart, Curr. Opin. Colloid Interf. Sci. 1998, 3, 150.
3. J. M. Lehn, Supramolecular Chemistry; Concepts and Perspectives, VCH, Weinheim, 1995; E. C. Constable, Metals and Ligand Reactivity: An Introduction to Organic Chemistry of Metal Complexes, VCH, Weinheim, 1995; F. M. Raymo, J. F. Stoddart, Curr. Opin. Colloid Interf. Sci. 1998, 3, 150.
4. J. C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, K. S. Suslick), Pergamon, Oxford, 1996, p. 43; D. B. Amabilino, F. M. Raymo, J. F. Stoddart in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, K. S. Suslick), Pergamon, Oxford, 1996, p. 85.
5. J. C. Chambron, C. O. Dietrich-Buchecker, J.-P. Sauvage in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, K. S. Suslick), Pergamon, Oxford, 1996, p. 43; D. B. Amabilino, F. M. Raymo, J. F. Stoddart in Comprehensive Supramolecular Chemistry, Vol. 9 (Eds.: J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, K. S. Suslick), Pergamon, Oxford, 1996, p. 85.
6. C. Piguet, G. Bernardinelli, G. Hopfgartner, Chem. Rev. 1997, 97, 2005; B. Hasenknopf, J. M. Lehn, N. Boumediene, A. Dupont-Gervais, A. Van Dorsselaer, B. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956.
7. C. Piguet, G. Bernardinelli, G. Hopfgartner, Chem. Rev. 1997, 97, 2005; B. Hasenknopf, J. M. Lehn, N. Boumediene, A. Dupont-Gervais, A. Van Dorsselaer, B. Kneisel, D. Fenske, J. Am. Chem. Soc. 1997, 119, 10956.
8. A. M. Garcia, F. J. Romero-Salguero, D. M. Bassani, J.-M. Lehn, G. Baum, D. Fenske, Chem. Eur. J. 1999, 5, 1803.
9. D. P. Funeriu, J. M. Lehn, G. Baum, D. Fenske, Chem. Eur. J. 1997, 3, 99; S. Leininger, B. Olenyuk, P. Stang, Chem. Rev. 2000, 100, 853.
10. D. P. Funeriu, J. M. Lehn, G. Baum, D. Fenske, Chem. Eur. J. 1997, 3, 99; S. Leininger, B. Olenyuk, P. Stang, Chem. Rev. 2000, 100, 853.
11. I. Weissbuch, P. N. W. Baxter, S. Cohen, H. Cohen, K. Kjaer, P. B. Howes, J. Als-Nielsen, G. S. Hanan, U. S. Schubert, J.-M. Lehn, L. Leiserowitz, M. Lahav, J. Am. Chem. Soc. 1998, 120, 4850.
12. L. A. Cuccia, J.-M. Lehn, J.-C. Homo, M. Schmutz, Angew. Chem. 2000, 112, 239; Angew. Chem. Int. Ed. Engl. 2000, 39, 233.
13. L. A. Cuccia, J.-M. Lehn, J.-C. Homo, M. Schmutz, Angew. Chem. 2000, 112, 239; Angew. Chem. Int. Ed. Engl. 2000, 39, 233.
14. Handbook of Liquid Crystals, Vol. 1-3 (Eds.: D. Demus, J. W. Goodby, H.-W. Spiess, V. Vill), Wiley-VCH, Weinheim, 1998.
15. Metallomesogens (Ed.: J. L. Serrano), VCH, Weinheim, 1996; B. Donnio, D. W. Bruce in Structure and Bonding 95: Liquid Crystals II (Ed.: D. M. P. Mingos). Springer, Berlin, 1999, p. 193.
16. Metallomesogens (Ed.: J. L. Serrano), VCH, Weinheim, 1996; B. Donnio, D. W. Bruce in Structure and Bonding 95: Liquid Crystals II (Ed.: D. M. P. Mingos). Springer, Berlin, 1999, p. 193.
17. K. Hanabusa, J.-I. Higashi, T. Koyama, H. Shira, N. Hojo, A. Kurose, Makromol. Chem. 1989, 190, 1.
18. T. Kuboki, K. Araki, M. Yamada, S. Shiraishi, Bull. Chem. Soc. Jpn. 1994, 67, 984.
19. D. W. Bruce, J. D. Holbrey, A. R. Tajbakhsh, G. J. T. Tiddy, J. Mater. Chem. 1993, 67, 984; J. D. Holbrey, G. J. T. Tiddy, D. W. Bruce, J. Chem. Soc. Dalton Trans. 1995, 1769.
20. D. W. Bruce, J. D. Holbrey, A. R. Tajbakhsh, G. J. T. Tiddy, J. Mater. Chem. 1993, 67, 984; J. D. Holbrey, G. J. T. Tiddy, D. W. Bruce, J. Chem. Soc. Dalton Trans. 1995, 1769.
21. F. Neve, M. Ghedini, A. Crispini, Chem. Commun. 1996, 2463; F. Neve, M. Ghedini, O. Francescangeli, S. Campagna, Liq. Cryst. 1998, 24, 673.
22. F. Neve, M. Ghedini, A. Crispini, Chem. Commun. 1996, 2463; F. Neve, M. Ghedini, O. Francescangeli, S. Campagna, Liq. Cryst. 1998, 24, 673.
23. E. C. Constable, C. E. Housecroft, Chimia 1998, 52, 533.
24. M. Ghedini, D. Pucci, J. Organomet. Chem. 1990, 395, 105.
25. D. W. Bruce, K. E. Rowe, Liq. Cryst. 1995, 18, 161; D. W. Bruce, K. E. Rowe, Liq. Cryst. 1996, 20, 183.
26. D. W. Bruce, K. E. Rowe, Liq. Cryst. 1995, 18, 161; D. W. Bruce, K. E. Rowe, Liq. Cryst. 1996, 20, 183.
27. L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1995, 18, 157; L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1996, 20, 235; A. El-ghayoury, L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, Liq. Cryst. 1996, 21, 143.
28. L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1995, 18, 157; L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1996, 20, 235; A. El-ghayoury, L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, Liq. Cryst. 1996, 21, 143.
29. L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1995, 18, 157; L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, E. Campillos, R. Deschenaux, Liq. Cryst. 1996, 20, 235; A. El-ghayoury, L. Douce, R. Ziessel, R. Seghrouchni, A. Skoulios, Liq. Cryst. 1996, 21, 143.
30. A. J. Attias, C. Cavalli, B. Bloch, J. Chim. Phys. 1998, 95, 1319; A. J. Attias, C. Cavalli, B. Bloch, N. Guillou, C. Noel, Chem. Mater. 1999, 11, 2057.
31. A. J. Attias, C. Cavalli, B. Bloch, J. Chim. Phys. 1998, 95, 1319; A. J. Attias, C. Cavalli, B. Bloch, N. Guillou, C. Noel, Chem. Mater. 1999, 11, 2057.
32. K. E. Rowe, D. W. Bruce, J. Chem. Soc. Dalton Trans. 1996, 3913.
33. K. E. Rowe, D. W. Bruce, J. Mater. Chem. 1998, 8, 331.
34. A. El-ghayoury, L. Douce, A. Skoulios, R. Ziessel, Angew. Chem. 1998, 110, 1303; Angew. Chem. Int. Ed. 1998, 37, 1255.
35. A. El-ghayoury, L. Douce, A. Skoulios, R. Ziessel, Angew. Chem. 1998, 110, 1303; Angew. Chem. Int. Ed. 1998, 37, 1255.
36. [15]
37. The polar groups of the amphiphilic anions should be located close to the central cores.
38. Related lamellocolumnar structures have been found in other classes of compounds: P. Davidson, A. M. Levelut, H. Strzelecka, V. Gionis, J. Phys. Fr. 1983, 44, L823; G. Lattermann, S. Schmidt, R. Kleppinger, J.- H. Wendorff, Adv. Mater. 1992, 4, 30; J. Malthête, A.-M. Levelut, L. Liebert, Adv. Mater. 1992, 4, 37; D. Haristoy, S. Mery, B. Heinrich, L. Mager, J. P. Nicoud, D. Guillon, Liq. Cryst. 2000, 27, 321.
39. Related lamellocolumnar structures have been found in other classes of compounds: P. Davidson, A. M. Levelut, H. Strzelecka, V. Gionis, J. Phys. Fr. 1983, 44, L823; G. Lattermann, S. Schmidt, R. Kleppinger, J.-H. Wendorff, Adv. Mater. 1992, 4, 30; J. Malthête, A.-M. Levelut, L. Liebert, Adv. Mater. 1992, 4, 37; D. Haristoy, S. Mery, B. Heinrich, L. Mager, J. P. Nicoud, D. Guillon, Liq. Cryst. 2000, 27, 321.
40. Related lamellocolumnar structures have been found in other classes of compounds: P. Davidson, A. M. Levelut, H. Strzelecka, V. Gionis, J. Phys. Fr. 1983, 44, L823; G. Lattermann, S. Schmidt, R. Kleppinger, J.- H. Wendorff, Adv. Mater. 1992, 4, 30; J. Malthête, A.-M. Levelut, L. Liebert, Adv. Mater. 1992, 4, 37; D. Haristoy, S. Mery, B. Heinrich, L. Mager, J. P. Nicoud, D. Guillon, Liq. Cryst. 2000, 27, 321.
41. Related lamellocolumnar structures have been found in other classes of compounds: P. Davidson, A. M. Levelut, H. Strzelecka, V. Gionis, J. Phys. Fr. 1983, 44, L823; G. Lattermann, S. Schmidt, R. Kleppinger, J.- H. Wendorff, Adv. Mater. 1992, 4, 30; J. Malthête, A.-M. Levelut, L. Liebert, Adv. Mater. 1992, 4, 37; D. Haristoy, S. Mery, B. Heinrich, L. Mager, J. P. Nicoud, D. Guillon, Liq. Cryst. 2000, 27, 321.
42. R. Ziessel, A. Harriman, J. Suffert, M.-T. Youinou, A. De Cian, J. Fischer, Angew. Chem. 1997, 109, 2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2509.
43. R. Ziessel, A. Harriman, J. Suffert, M.-T. Youinou, A. De Cian, J. Fischer, Angew. Chem. 1997, 109, 2621; Angew. Chem. Int. Ed. Engl. 1997, 36, 2509.
44. A. El-ghayoury, L. Douce, A. Skoulios, R. Ziessel, Angew. Chem. 1998, 110, 2327; Angew. Chem. Int. Ed. 1998, 37, 2205.
45. A. El-ghayoury, L. Douce, A. Skoulios, R. Ziessel, Angew. Chem. 1998, 110, 2327; Angew. Chem. Int. Ed. 1998, 37, 2205.
46. R. Ziessel, L. Douce, A. El-ghayoury, A. Harriman, A. Skoulios, Angew. Chem. 2000, 112, 1549; Angew. Chem. Int. Ed. 2000, 39, 1489.
47. R. Ziessel, L. Douce, A. El-ghayoury, A. Harriman, A. Skoulios, Angew. Chem. 2000, 112, 1549; Angew. Chem. Int. Ed. 2000, 39, 1489.
48. L. Douce, A. El-ghayoury, A. Skoulios, R. Ziessel, Chem. Commun. 1999, 2033.
49. H. T. Nguyen, C. Destrade, J. Malthete, Adv. Mater. 1997, 9, 375.
50. D. W. Bruce, B. Donnio, D. Guillon, B. Heinrich, M. Ibn-Elhaj, Liq. Cryst. 1995, 19, 537; B. Donnio, D. W. Bruce, New J. Chem. 1999, 275.
51. D. W. Bruce, B. Donnio, D. Guillon, B. Heinrich, M. Ibn-Elhaj, Liq. Cryst. 1995, 19, 537; B. Donnio, D. W. Bruce, New J. Chem. 1999, 275.
52. Metallomesogens with an octahedral central core have also been reported: A.-M. Giroud-Godquin, A. Rassat, C. R. Acad. Sci. Ser. 2 1982, 294, 241; H. Zheng, T. M. Swager, J. Am. Chem. Soc. 1994, 111, 761; S. T. Trzaska, H.-F. Hsu, T. M. Swager, J. Am. Chem. Soc. 1999, 121, 4518.
53. Metallomesogens with an octahedral central core have also been reported: A.-M. Giroud-Godquin, A. Rassat, C. R. Acad. Sci. Ser. 2 1982, 294, 241; H. Zheng, T. M. Swager, J. Am. Chem. Soc. 1994, 111, 761; S. T. Trzaska, H.-F. Hsu, T. M. Swager, J. Am. Chem. Soc. 1999, 121, 4518.
54. Metallomesogens with an octahedral central core have also been reported: A.-M. Giroud-Godquin, A. Rassat, C. R. Acad. Sci. Ser. 2 1982, 294, 241; H. Zheng, T. M. Swager, J. Am. Chem. Soc. 1994, 111, 761; S. T. Trzaska, H.-F. Hsu, T. M. Swager, J. Am. Chem. Soc. 1999, 121, 4518.
55. A. Pegenau, P. Göring, C. Tschierske, Chem. Commun. 1996, 2563; A. Pegenau, P. Göring, S. Diele, C. Tschierske, Chem. Eur. J. 1999, 5, 1643.
56. A. Pegenau, P. Göring, C. Tschierske, Chem. Commun. 1996, 2563; A. Pegenau, P. Göring, S. Diele, C. Tschierske, Chem. Eur. J. 1999, 5, 1643.
57. J. Malthête, New. J. Chem. 1996, 20, 925.
58. A. Pegenau, X. H. Cheng, C. Tschierske, S. Diele, New J. Chem. 1999, 23, 465; X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605; Angew. Chem. Int. Ed. 2000, 39, 592.
59. A. Pegenau, X. H. Cheng, C. Tschierske, S. Diele, New J. Chem. 1999, 23, 465; X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605; Angew. Chem. Int. Ed. 2000, 39, 592.
60. A. Pegenau, X. H. Cheng, C. Tschierske, S. Diele, New J. Chem. 1999, 23, 465; X. H. Cheng, S. Diele, C. Tschierske, Angew. Chem. 2000, 112, 605; Angew. Chem. Int. Ed. 2000, 39, 592.
61. C. Tschierske, J. Mater. Chem. 1998, 8, 1485.
62. C. M. Paleos, Mol. Cryst. Liq. Cryst. 1994, 243, 159; J. Charvolin, J. Chim. Phys. 1983, 80, 15.
63. C. M. Paleos, Mol. Cryst. Liq. Cryst. 1994, 243, 159; J. Charvolin, J. Chim. Phys. 1983, 80, 15.
64. T. Salditt, I. Koltover, J. O. Rädler, C. R. Safinya, Phys. Rev. Lett. 1997, 79, 2582; C. R. Safinya, I. Koltover, J. Raedler, Curr. Opin. Colloid Interf. Sci. 1998, 3, 69; C. S. O'Hern, T. C. Lubensky, Phys. Rev. Lett. 1998, 80, 4354.
65. T. Salditt, I. Koltover, J. O. Rädler, C. R. Safinya, Phys. Rev. Lett. 1997, 79, 2582; C. R. Safinya, I. Koltover, J. Raedler, Curr. Opin. Colloid Interf. Sci. 1998, 3, 69; C. S. O'Hern, T. C. Lubensky, Phys. Rev. Lett. 1998, 80, 4354.
66. T. Salditt, I. Koltover, J. O. Rädler, C. R. Safinya, Phys. Rev. Lett. 1997, 79, 2582; C. R. Safinya, I. Koltover, J. Raedler, Curr. Opin. Colloid Interf. Sci. 1998, 3, 69; C. S. O'Hern, T. C. Lubensky, Phys. Rev. Lett. 1998, 80, 4354.
67. A. R. A. Palmans, J. A. J. M. Vekemans, H. Fischer, R. A. Hikmet, E. W. Meijer, Chem. Eur. J. 1997, 3, 300; A. R. A. Palmans, J. A. J. M. Vekemans, R. A. Hikmet, H. Fischer, R. W. Meijer, Adv. Mater. 1998, 10, 873.
68. A. R. A. Palmans, J. A. J. M. Vekemans, H. Fischer, R. A. Hikmet, E. W. Meijer, Chem. Eur. J. 1997, 3, 300; A. R. A. Palmans, J. A. J. M. Vekemans, R. A. Hikmet, H. Fischer, R. W. Meijer, Adv. Mater. 1998, 10, 873.