Synthesis and columnar mesophase of fluorescent liquid crystals bearing a C2-symmetric chiral core

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4069-4072

  Yang, Chia Wei ^a   Hsia, Tsai Hua ^b   Chen, G Chung ^b   Lai, Chung Kung ^b   Liu, Rai Shung ^a  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61349084773     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801561b     Document Type: Article

References (35)

1. Demus, D.; Goodby, J.; Gray, G. W.; Spiess, H.-W.; Vill, V. Handbook of Liquid Crystals: Fundamentals; Wiley-VCH: Weinheim, 1998; Vol. 1, Chapter 5.
2. Recent review for columnar liquid crystals, see: Laschat, S.; Baro, A.; Steinke, N.; Giesselmann, F.; Hagele, C.; Scalia, G.; Judele, R.; Kapatsina, E.; Sauer, S.; Schreivogel, A.; Tosoni, M. Angew. Chem., Int. Ed. 2007, 46, 4832.
3. (a) Feng, X.; Pisula, W.; Zhi, L.; Takase, M.; Müllen, K. Angew. Chem., Int. Ed. 2008, 47, 1.
4. (b) Feng, X.; Pisula, W.; Müllen, K. J. Am. Chem. Soc. 2007, 129, 14116.
5. (a) Yelamaggad, C. V.; Achalkumar, A. S.; Rao, D. S. S.; Prasad, S. K. J. Mater. Chem. 2007, 17, 4521.
6. (b) Percec, V.; Aqad, E.; Peterca, M.; Rudick, J. G.; Lemon, L.; Ronda, J. C.; De, B. B.; Heiney, P. A.; Meijer, E. W. J. Am. Chem. Soc. 2006, 128, 16365.
7. (c) Barbera, J.; Puig, L.; Romero, P.; Serrano, J. L.; Sierra, T. J. Am. Chem. Soc. 2006, 128, 4487.
8. (d) Mateos-Timoneda, M. A.; Crego-Calama, M.; Reinhoudt, D. N. Chem.-Eur. J. 2006, 12, 2630.
9. (a) Barbera, J.; Iglesias, R.; Serrano, J. L.; Sierra, T.; de la Fuente, M. R.; Palacios, B.; Perez-Jubindo, M. A.; Vazquez, J. T. J. Am. Chem. Soc. 1998, 120, 2908.
10. (b) Scherowsky, G.; Chen, X. H. Liq. Cryst. 1994, 17, 803.
11. (c) Bock, H.; Helfrich, W. Liq. Cryst. 1995, 18, 707.
12. (d) Bock, H; Helfrich, W. Liq. Cryst. 1995, 18, 387.
13. Verbiest, T.; Elshocht, S. V.; Kauranen, M.; Hellemans, L.; Snauwaert, J.; Nuckolls, C.; Katz, T. J.; Persoons, A. Science 1998, 282, 913.
14. (a) Mukkamala, R.; Burns, C. L., Jr.; Catchings, R. M., III; Weiss, R. G J. Am. Chem. Soc. 1996, 118, 9498, and references therein.
15. (b) Kohne, B.; Pracfcke, K. Angew. Chem., Int. Ed. 1984, 23, 82.
16. (c) Malthête, J.; Collet, A. J. Am. Chem. Soc. 1987, 109, 7544.
17. (d) Nuckolls, C.; Katz, T. J. J. Am. Chem. Soc. 1998, 120, 9541.
18. (e) Barberá, J.; Cavero, E.; Lehmann, M.; Serrano, J.-L.; Sierra, T.; Vázquez, J. T. J. Am. Chem. Soc. 2003, 125, 4527.
19. Binap in asymmetric catalysis, see: (a) Knowles, W. S.; Noyori, R. Acc. Chem. Res. 2007, 40, 1238.
20. (b) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
21. Very few examples are known for chiral fluorescent liquid crystals. See ref 7d: Fechtenkötter, A.; Tchebotareva, N.; Watson, M.; Müllen, K. Tetrahedron 2001, 57, 3769.
22. -1.
23. (a) Jones, B. A.; Facchetti, A.; Wasielewski, M. R.; Marks, T. J. J. Am. Chem. Soc. 2007, 129, 15259.
24. (b) Foster, E. J.; Jones, R. B.; Lavigueur, C.; Williams, V. E. J. Am. Chem. Soc. 2006, 128, 8569.
25. (c) Debije, M. G.; Chen, Z. J.; Piris, J.; Neder, R. B.; Watson, M. M.; Müllen, K.; Wurthner, F. J. Mater. Chem. 2005, 15, 1270.
26. (d) Eichhorn, S. H.; Paraskos, A. J.; Kishikawa, K.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 12742.
27. (e) Kishikawa, K.; Furusawa, S.; Yamaki, T.; Kohmoto, S.; Yamamoto, M.; Yamaguchi, K. J. Am. Chem. Soc. 2002, 124, 1597.
28. Chen, R.; Qian, C.; de Vries, J. G. Tetrahedron Lett. 2001, 42, 6919.
29. Ames, D. E.; Opalko, A. Tetrahedron 1984, 40, 1919.
30. Lightner, D. A.; Gurst, J. E., Organic Conformational Analysis and Stereochemistry form Circular Dichroism Spectroscopy; Wiley-VCH: Weinheim, 2000; Chapter 14.
31. 23 = -57.2) of the authentic sample. This information shows negligible loss of enantiopurity, and even the sample was pretreated at 110 °C.
32. Fontes, E.; Heiney, P. A.; Ohba, M.; Haseltine, J. N.; Smith. A. B., III. Phys. Rev. A. 1988, 37, 1329.
33. 2-symmetric chiral compounds were often used as a dopant 18 rather than a building block to form liquid crystals.
34. (a) Boulton, C. J.; Finden, J. G.; Yuh, E.; Sutherland. J. J.; Wand, M. D.; Wu, G.; Lemieux, R. P. J. Am. Chem. Soc. 2005, 127, 13656.
35. (b) Pijper, D.: Jongejan, M. G. M.; Meetsma, A.; Feringa, B. L. J. Am. Chem. Soc. 2008, 130, 4541.