Control of single crystal structure and liquid crystal phase behaviour via arene-perfluoroarene interactions

Chemical Communications

Volumn , Issue 24, 1999, Pages 2493-2494

  Dai, Chaoyang ^a   Nguyen, Paul ^a   Marder, Todd B ^a,b   Scott, Andrew J ^c   Clegg, William ^c   Viney, Christopher ^d,e  

^a UNIVERSITY OF WATERLOO   (Canada)

^b DURHAM UNIVERSITY   (United Kingdom)

^c NEWCASTLE UNIVERSITY   (United Kingdom)

^d UNIVERSITY OF OXFORD   (United Kingdom)

^e HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PERFLUORO COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; LIQUID CRYSTAL; MOLECULAR INTERACTION; PHASE TRANSITION;

EID: 0033592922     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906199a     Document Type: Article

References (30)

1. C. A. Hunter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1584; Chem. Soc. Rev., 1994, 23, 101.
2. C. A. Hunter, Angew. Chem., Int. Ed. Engl., 1993, 32, 1584; Chem. Soc. Rev., 1994, 23, 101.
3. P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J. A. Preece, J. F. Stoddart, M. S. Tolly, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31; K. Ochai, Y. Mazaki, S. Nashikiori, K. Kobayashi and S. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1996, 1139; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg and S. Treat, Chem. Commun., 1997, 897; J. E. Kickham, S. J. Loeb and S. L. Murphy, Chem. Eur. J., 1997, 3, 1203.
4. P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J. A. Preece, J. F. Stoddart, M. S. Tolly, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31; K. Ochai, Y. Mazaki, S. Nashikiori, K. Kobayashi and S. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1996, 1139; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg and S. Treat, Chem. Commun., 1997, 897; J. E. Kickham, S. J. Loeb and S. L. Murphy, Chem. Eur. J., 1997, 3, 1203.
5. P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J. A. Preece, J. F. Stoddart, M. S. Tolly, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31; K. Ochai, Y. Mazaki, S. Nashikiori, K. Kobayashi and S. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1996, 1139; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg and S. Treat, Chem. Commun., 1997, 897; J. E. Kickham, S. J. Loeb and S. L. Murphy, Chem. Eur. J., 1997, 3, 1203.
6. P. R. Ashton, J. Huff, S. Menzer, I. W. Parsons, J. A. Preece, J. F. Stoddart, M. S. Tolly, A. J. P. White and D. J. Williams, Chem. Eur. J., 1996, 2, 31; K. Ochai, Y. Mazaki, S. Nashikiori, K. Kobayashi and S. Hayashi, J. Chem. Soc., Perkin Trans. 2, 1996, 1139; D. G. Hamilton, J. K. M. Sanders, J. E. Davies, W. Clegg and S. Treat, Chem. Commun., 1997, 897; J. E. Kickham, S. J. Loeb and S. L. Murphy, Chem. Eur. J., 1997, 3, 1203.
7. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, New York, 1989; Chem. Commun., 1997, 1475.
8. G. R. Desiraju, Crystal Engineering: The Design of Organic Solids, Elsevier, New York, 1989; Chem. Commun., 1997, 1475.
9. D. Adam, P. Schuhmaker, J. Simmerer, L. Häusslling, K. Slemensmeyer, K. H. Etzbach, H. Ringsdorf and D. Haarer, Nature, 1994, 371, 141; J. Zhang and J. S. Moore, J. Am. Chem. Soc., 1994, 116, 2655; K. M. Lee, C. K. Lee and I. J. B. Lin, Angew. Chem., Int. Ed. Engl., 1997, 36, 1850.
10. D. Adam, P. Schuhmaker, J. Simmerer, L. Häusslling, K. Slemensmeyer, K. H. Etzbach, H. Ringsdorf and D. Haarer, Nature, 1994, 371, 141; J. Zhang and J. S. Moore, J. Am. Chem. Soc., 1994, 116, 2655; K. M. Lee, C. K. Lee and I. J. B. Lin, Angew. Chem., Int. Ed. Engl., 1997, 36, 1850.
11. D. Adam, P. Schuhmaker, J. Simmerer, L. Häusslling, K. Slemensmeyer, K. H. Etzbach, H. Ringsdorf and D. Haarer, Nature, 1994, 371, 141; J. Zhang and J. S. Moore, J. Am. Chem. Soc., 1994, 116, 2655; K. M. Lee, C. K. Lee and I. J. B. Lin, Angew. Chem., Int. Ed. Engl., 1997, 36, 1850.
12. C. R. Patrick and G. S. Prosser, Nature, 1960, 187, 1021. For a recent theoretical study see: A.P. West Jr., S. Mecozzi and D. Dougherty, J. Phys. Org. Chem., 1997, 10, 347.
13. C. R. Patrick and G. S. Prosser, Nature, 1960, 187, 1021. For a recent theoretical study see: A.P. West Jr., S. Mecozzi and D. Dougherty, J. Phys. Org. Chem., 1997, 10, 347.
14. J. H. Williams, Acc. Chem. Res., 1993, 26, 593.
15. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1997, 36, 248; G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 3641. See also: M. L. Renak, G. P. Bartholemew, S. Wang, P. J. Ricatto, R. J. Lachicotte and G. C. Bazan, J. Am. Chem. Soc., 1999, 121, 7787.
16. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1997, 36, 248; G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 3641. See also: M. L. Renak, G. P. Bartholemew, S. Wang, P. J. Ricatto, R. J. Lachicotte and G. C. Bazan, J. Am. Chem. Soc., 1999, 121, 7787.
17. G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1997, 36, 248; G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky and R. H. Grubbs, J. Am. Chem. Soc., 1998, 120, 3641. See also: M. L. Renak, G. P. Bartholemew, S. Wang, P. J. Ricatto, R. J. Lachicotte and G. C. Bazan, J. Am. Chem. Soc., 1999, 121, 7787.
18. P. Nguyen, Z. Yuan, L. Agocs, G. Lesley and T. B. Marder, Inorg. Chim. Acta, 1994, 220, 289; P. Nguyen, G. Lesley, C. Dai, N. J. Taylor, T. B. Marder, C. Viney, I. Ledoux and J. Zyss, in Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials, ed. J. F. Harrod and R. M. Laine, Kluwer, Dordrecht, 1995, p. 333; M. S. Khan, A. K. Kakkar, N. J. Long, J. Lewis, P. Raithby, P. Nguyen, T. B. Marder, F. Wittmann and R. H. Friend, J. Mater. Chem., 1994, 4, 1227; P. Nguyen, G. Lesley, T. B. Marder, I. Ledoux and J. Zyss, Chem. Mater., 1997, 9, 406 and references therein.
19. P. Nguyen, Z. Yuan, L. Agocs, G. Lesley and T. B. Marder, Inorg. Chim. Acta, 1994, 220, 289; P. Nguyen, G. Lesley, C. Dai, N. J. Taylor, T. B. Marder, C. Viney, I. Ledoux and J. Zyss, in Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials, ed. J. F. Harrod and R. M. Laine, Kluwer, Dordrecht, 1995, p. 333; M. S. Khan, A. K. Kakkar, N. J. Long, J. Lewis, P. Raithby, P. Nguyen, T. B. Marder, F. Wittmann and R. H. Friend, J. Mater. Chem., 1994, 4, 1227; P. Nguyen, G. Lesley, T. B. Marder, I. Ledoux and J. Zyss, Chem. Mater., 1997, 9, 406 and references therein.
20. P. Nguyen, Z. Yuan, L. Agocs, G. Lesley and T. B. Marder, Inorg. Chim. Acta, 1994, 220, 289; P. Nguyen, G. Lesley, C. Dai, N. J. Taylor, T. B. Marder, C. Viney, I. Ledoux and J. Zyss, in Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials, ed. J. F. Harrod and R. M. Laine, Kluwer, Dordrecht, 1995, p. 333; M. S. Khan, A. K. Kakkar, N. J. Long, J. Lewis, P. Raithby, P. Nguyen, T. B. Marder, F. Wittmann and R. H. Friend, J. Mater. Chem., 1994, 4, 1227; P. Nguyen, G. Lesley, T. B. Marder, I. Ledoux and J. Zyss, Chem. Mater., 1997, 9, 406 and references therein.
21. P. Nguyen, Z. Yuan, L. Agocs, G. Lesley and T. B. Marder, Inorg. Chim. Acta, 1994, 220, 289; P. Nguyen, G. Lesley, C. Dai, N. J. Taylor, T. B. Marder, C. Viney, I. Ledoux and J. Zyss, in Applications of Organometallic Chemistry in the Preparation and Processing of Advanced Materials, ed. J. F. Harrod and R. M. Laine, Kluwer, Dordrecht, 1995, p. 333; M. S. Khan, A. K. Kakkar, N. J. Long, J. Lewis, P. Raithby, P. Nguyen, T. B. Marder, F. Wittmann and R. H. Friend, J. Mater. Chem., 1994, 4, 1227; P. Nguyen, G. Lesley, T. B. Marder, I. Ledoux and J. Zyss, Chem. Mater., 1997, 9, 406 and references therein.
22. Liquid Crystals - Applications and Uses, ed. B. Bahadur, World Scientific, Singapore, 1990, vol. 1.
23. R. J. Twieg, V. Chu, C. Nguyen, C. Dannels and C. Viney, Liq. Cryst., 1996, 20, 287.
24. W. Maier and A. Saupe, Z. Naturforsch., Teil A, 1959, 14, 882.
25. C. T. Imrie, Trends Polym. Sci., 1997, 3, 22; C. Viney, Supramol. Sci., 1997, 4, 75; A. E. Huber and C. Viney, Phys. Rev. Lett., 1998, 80, 623.
26. C. T. Imrie, Trends Polym. Sci., 1997, 3, 22; C. Viney, Supramol. Sci., 1997, 4, 75; A. E. Huber and C. Viney, Phys. Rev. Lett., 1998, 80, 623.
27. C. T. Imrie, Trends Polym. Sci., 1997, 3, 22; C. Viney, Supramol. Sci., 1997, 4, 75; A. E. Huber and C. Viney, Phys. Rev. Lett., 1998, 80, 623.
28. T. Kato, Y. Kubota, M. Nakano and T. Uryu, Chem. Lett., 1995, 1127; H. Kihara, T. Kato, T. Uryu, S. Ujiie, U. Kumar, J. M. J. Fréchet, D. W. Bruce and D. J. Price, Liq. Cryst., 1996, 21, 25.
29. T. Kato, Y. Kubota, M. Nakano and T. Uryu, Chem. Lett., 1995, 1127; H. Kihara, T. Kato, T. Uryu, S. Ujiie, U. Kumar, J. M. J. Fréchet, D. W. Bruce and D. J. Price, Liq. Cryst., 1996, 21, 25.
30. After our paper was submitted, Grubbs et al. reported the use of areneperfluoroarene interactions to stabilise discotic LC phases: M. Weck, A. R. Dunn, K. Matsumoto, G. W. Coates, E. B. Lobkovsky and R. H. Grubbs, Angew. Chem., Int. Ed., 1999, 38, 2741.