Ferroelectric liquid crystals induced by dopants with axially chiral 2,2′-spirobiindan-1,1′-dione cores

Journal of the American Chemical Society

Volumn 127, Issue 39, 2005, Pages 13656-13665

  Boulton, Christopher J ^a   Finden, Jeremy G ^a   Yuh, Eagranie ^a   Sutherland, Jeffrey J ^a   Wand, Michael D ^b   Wu, Gang ^a   Lemieux, Robert P ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b Displaytech Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; COMPLEXATION; DERIVATIVES; DOPING (ADDITIVES); KETONES; LIQUID CRYSTALS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLARIZATION;

AXIAL COMPOUNDS; CHIRAL COMPOUNDS; DOPANTS; FERROELECTRIC LIQUID CRYSTALS;

FERROELECTRIC MATERIALS;

2',3' DIFLUORO 4 HEPTYL 4'' NONYL 4 TERPHENYL DERIVATIVE; 2,2' SPIROBIINDAN 1,1' DIONE; 4 [4' HEPTYL(1,1' BIPHEN) 4YL] 1 HEXYLCYCLOHEXANECARBONITRILE; 5,5' DIHEPTYLOXY 2,2' SPIROBIINDAN 1,1' DIONE; 5,6' DIHEPTYLOXY 2,2' SPIROBIINDAN 1,1' DIONE; 6,6' DIHEPTYLOXY 2,2' SPIROBIINDAN 1,1' DIONE; CYCLOHEXANE DERIVATIVE; FUNCTIONAL GROUP; INDAN DERIVATIVE; SPIRO COMPOUND; TERPHENYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATION; DEUTERON NUCLEAR MAGNETIC RESONANCE; ELECTRICITY; ISOMER; LIQUID CRYSTAL; MOLECULAR INTERACTION; MOLECULAR MODEL; OPTICAL ROTATION; PLOTS AND CURVES; POLARIZATION; RACEMIC MIXTURE; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 25844451207     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054322k     Document Type: Article

References (58)

1. (a) Proni, G.; Spada, G. P. Enantiomer 2001, 6, 171.
2. (b) di Matteo, A.; Todd, S. M.; Gottarelli, G.; Solladié, G.; Williams, V. E.; Lemieux, R. P.; Ferrarini, A.; Spada, G. P. J. Am. Chem. Soc. 2001, 123, 7842.
3. Lemieux, R. P. Acc. Chem. Res. 2001, 34, 845.
4. Hegmann, T.; Meadows, M. R.; Wand, M. D.; Lemieux, R. P. J. Mater. Chem. 2004, 14, 185.
5. (a) Lagerwall, S. T. Ferroelectric and Antiferroelectric Liquid Crystals: Wiley-VCH: Weinheim, 1999.
6. (b) Lagerwall, S. T. In Handbook of Liquid Crystals; Demus, D., Goodby, J. W., Gray, G. W., Spiess, H. W., Vill, V., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 2B.
7. (c) Walba, D. M. Science 1995, 270, 250.
8. (d) Clark, N. A.; Lagerwall, S. T. In Ferroelectric Liquid Crystals: Principles, Properties and Applications; Goodby, J. W., Blinc, R., Clark, N. A., Lagerwall, S. T., Osipov, M. A., Pikin, S. A., Sakurai, T., Yoshino, K., Zeks, B., Eds.; Gordon and Breach: Philadelphia, 1991; pp 409-452.
9. (e) Dijon, J. In Liquid Crystals: Applications and Uses; Bahadur, B., Ed.; World Scientific: Singapore, 1990; Vol. 1, Chapter 13.
10. (a) Walba, D. M.; Xiao, L.; Keller, P.; Shao, R.; Link, D.; Clark, N. A. Pure Appl. Chem. 1999, 71, 2117.
11. (b) Walba, D. M.; Dyer, D. J.; Sierra, T.; Cobben, P. L.; Shao, R. F.; Clark, N. A. J. Am. Chem. Soc. 1996, 118, 1211.
12. (c) Walba, D. M.; Ros, M. B.; Clark, N. A.; Shao, R. F.; Robinson, M. G.; Liu, J. Y.; Johnson, K. M.; Doroski, D. J. Am. Chem. Soc. 1991, 113, 5471.
13. Grassland, W. A.; Wilkinson, T. D. In Handbook of Liquid Crystals; Demus, D., Goodby, J. W., Gray, G. W., Spiess, H.-W., Vill, V., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, p 763.
14. Ikeda, T.; Kanazawa, A. In Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, 2001; p 363.
15. Lemieux, R. P. Chem. Rec. 2004, 3, 288.
16. Walba, D. M. In Advances in the Synthesis and Reactivity of Solids; Mallouck, T. E., Ed.; JAI Press Ltd.: Greenwich, CT, 1991; Vol. 1, p 173.
17. (a) Glaser, M. A.; Clark, N. A.; Walba, D. M.; Keyes, M. P.; Radcliffe, M. D.; Snustad, D. C. Liq. Cryst. 2002, 29, 1073.
18. (b) Glaser, M. A. In Advances in the Computer Simulations of Liquid Crystals; Zannoni, C., Pasini, P., Eds.; Kluwer: Dordrecht, 1999; p 263.
19. Goodby, J. W. In Ferroelectric Liquid Crystals: Principles, Properties and Applications; Goodby, J. W., Blinc, R., Clark, N. A., Lagerwall, S. T., Osipov, M. A., Pikin, S. A., Sakurai, T., Yoshino, K., Zeks, B., Eds.; Gordon & Breach: Philadelphia, 1991; p 99.
20. Siemensmeyer, K.; Stegemeyer, H. Chem. Phys. Leu. 1988, 148, 409.
21. Kuczynski, W.; Stegemeyer, H. Chem. Phys. Lett. 1980, 70, 123.
22. Osipov, M. A.; Stegemeyer, H.; Sprick, A. Phys. Rev. E 1996, 54, 6387.
23. Stegemeyer, H.; Meister, R.; Hoffmann, U.; Sprick, A.; Becker, A. J. Mater. Chem. 1995, 5, 2183.
24. Tschierske, C. J. Mater. Chem. 1998, 8, 1485.
25. For a related example of molecular recognition via core-core interactions in SmC* liquid crystals, see: (a) Yoshizawa, A.; Nishiyama, I. Mol. Cryst. Liq. Cryst. 1995, 260, 403.
26. (b) Nishiyama, I.; Ishizika, H.; Yoshizawa, A. Ferroelectrics 1993, 147, 193.
27. Vizitiu, D.; Lazar, C.; Halden, B. J.; Lemieux, R. P. J. Am. Chem. Soc. 1999, 121, 8229.
28. Hartley, C. S.; Lazar, C.; Wand, M. D.; Lemieux, R. P. J. Am. Chem. Soc. 2002, 124, 13513.
29. 9
30. Vizitiu, D.; Lazar, C.; Radke, J. P.; Hartley, C. S.; Glaser, M. A.; Lemieux, R. P. Chem. Mater. 2001, 13, 1692.
31. For a preliminary communication, see: Boulton, C. J.; Sutherland, J. J.; Lemieux, R. P. J. Mater. Chem. 2003, 13, 644.
32. Nieman, J. A.; Keay, B. A. Tetrahedron: Asymmetry 1995, 6, 1575.
33. (a) Berova, N.; Nakanishi, K. In Exciton Chirality Methods: Principles and Applications; Berova, N., Nakanishi, K., Woody, R. W., Eds.; Wiley-VCH: New York, 2000.
34. (b) Harada, N.; Nakanishi, K. Circular Dichroic Spectroscope: Exciton Coupling in Organic Photochemistry, University Science Books: New York, 1983.
35. Falk, H.; Frostl, W.; Hofer, O.; Schlögl, K. Monatsh. Chem. 1974, 105, 598.
36. Langer, E.; Lehner, H.; Neudeck, H.; Schlögl, K. Monatsh. Chem. 1978, 109, 987.
37. (a) Zerner, M. C. In Review in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: New York, 1991; pp 313-366.
38. (b) Ridley, J. E.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111.
39. Dynesen, E. Acta Chem. Scand., Ser. B 1975, 29, 77.
40. This approach was used to determine the absolute configuration of unsubstituted 2,2′-spirobiindan-1,1′-dione: Harada, N.; Ai, T.; Uda, H. J. Chem. Soc., Chem. Commun. 1982, 232.
41. Dong, R. Y. In Encyclopedia of Nuclear Magnetic Resonance; Grant, D. M., Harris, R. K., Eds.; John Wiley & Sons: 1996; Vol. 4, pp 2752-2760.
42. (a) Workentin, M. S.; Leigh, W. J. J. Phys. Chem. 1992, 96, 9666.
43. (b) Workentin, M. S.; Fahie, B. J.; Leigh, W. J. Can. J. Chem. 1991, 69, 1435.
44. (c) Workentin, M. S.; Leigh, W. J.; Jeffrey, K. R. J. Am. Chem. Soc. 1990, 112, 7329.
45. (d) Fahie, B. J.; Mitchell, D. S.; Leigh, W. J. Can. J. Chem. 1989, 67, 148.
46. (e) Fahie, B. J.; Mitchell, D. S.; Workentin, M. S.; Leigh, W. J. J. Am. Chem. Soc. 1989, 111, 2916.
47. (a) Vlahakis, J. Z.; Lemieux, R. P. J. Mater. Chem. 2004, 14, 1486.
48. (b) Maly, K. E.; Wu, G.; Lemieux, R. P. Liq. Cryst. 2001, 28, 457.
49. Czarniecka, K.; Samulski, E. T. Mol. Cryst. Liq. Cryst. 1981, 63, 205.
50. (a) Emsley, J. W.; Lesot, P.; Courtieu, J.; Merlet, D. Phys. Chem. Chem. Phys. 2004, 6, 5331.
51. (b) Merlet, D.; Loewenstein, A.; Smadja, W.; Courtieu, J.; Lesot, P. J. Am. Chem. Soc. 1998, 120, 963.
52. (c) Meddour, A.; Canet, I.; Loewenstein, A.; Péchiné, J. M.; Courtieu, J. J. Am. Chem. Soc. 1994, 116, 9652.
53. Miyasato, K.; Abe, S.; Takezoe, H.; Fukuda, A.; Kuze, E. Jpn. J. Appl. Phys. 1983, 22, L661.
54. 9 More rigorous analyses based on atomistic molecular dynamics simulations are currently under development: Ghenea, R.; Cann, N. M., unpublished results.
55. A related Monte Carlo molecular simulation method that calculates helical twisting powers based on fully atomistic structures of chiral dopants in a Gay-Berne nematic liquid crystal solvent has recently been reported: Earl, D. J.; Wilson, M. R. J. Chem. Phys. 2004, 120, 9679.
56. The two conformations in each degenerate pair can be interconverted by a 180° rotation about the polar axis.
57. The reason P3 would be favored over P3′ in three of the four hosts remains unclear. In conformation P3′, the 6-heptyloxyindanone fragment is oriented perpendicular to the tilt plane, which may be less compatible with the SmC binding site than the 5-heptyloxyindanone fragment in the same orientation. Interestingly, the perpendicular orientation of the 6-heptyloxyindanone fragment is also present in P4, but it cannot be avoided, as in (R)-3, by switching to another zigzag P conformation. This would be consistent with the remarkably low miscibility of (R)-4 relative to (R)-3 and (R)-1.
58. 2 was reported for a derivative of 2-hydroxy-5,5-dialkyl-δ-valerolactone: Sakashita, K.; Ikemoto, T.; Nakaoka, Y.; Terada, F.; Sako, Y.; Kageyama, Y.; Mori, K. Liq. Cryst. 1993, 13, 71.