Spontaneous chirality induction and enantiomer separation in liquid crystals composed of achiral rod-shaped 4-arylbenzoate esters

Journal of the American Chemical Society

Volumn 131, Issue 41, 2009, Pages 15055-15060

  Hyeon, Su Jeong ^a   Tanaka, Shingo ^b   Dong, Ki Yoon ^a,d   Choi, Suk Won ^b,c   Yun, Ho Kim ^a   Kawauchi, Susumu ^b   Araoka, Fumito ^b   Takezoe, Hideo ^b   Jung, Hee Tae ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^c Kyung Hee University   (South Korea)

^d UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CD SIGNALS; CD SPECTROSCOPY; CHIRALITY INDUCTIONS; CIRCULAR DICHROISM; CONFORMATIONAL CHANGE; ENANTIOMER SEPARATION; ENANTIOMERIC SEPARATION; EQUAL PROBABILITY; ESTER MOIETIES; FREELY SUSPENDED FILM; INDUCED CHIRALITY; ROD-SHAPED; ROD-SHAPED MOLECULES; SMECTIC ORDER; SMECTIC-A; SOFT CRYSTALS; SURFACE EFFECT; THEORETICAL CALCULATIONS;

CHIRALITY; DATA STORAGE EQUIPMENT; DICHROISM; ENANTIOMERS; ESTERIFICATION; LIQUID CRYSTALS; STEREOCHEMISTRY;

ESTERS;

4 BENZOATE ESTER DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CIRCULAR DICHROISM; CONFORMATIONAL TRANSITION; CRYSTALLIZATION; ENANTIOMER; LIQUID CRYSTAL;

EID: 70350067892     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja905785d     Document Type: Article

References (29)

1. Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palachios, J. C. Chem. Commun. 2000, 88, 7-892.
2. Perez-Garcia, L.; Amabilino, D. B. Chem. Soc. Rev. 2002, 31, 342-356.
3. Pasteur, L. Ann. Chim. Phys. 1848, 24, 442.
4. Fasel, R.; Parschau, M.; Ernst, K.-H. Nature 2006, 439, 449-452.
5. Takanishi, Y.; Takezoe, H.; Suzuki, Y.; Kobayashi, I.; Yajima, T.; Terada, M.; Mikami, K. Angew. Chem., Int. Ed. 1999, 38, 2353-2356.
6. Niori, T.; Sekine, T.; Watanabe, J.; Furukawa, T.; Takezoe, H. J. Mater. Chem. 1996, 6, 1231-1233.
7. Takezoe, H.; Takanishi, Y. Jpn. J. Appl. Phys. 2006, 45, 597-625.
8. Link, D. R.; Natale, G.; Shao, R.; Maclennan, J. E.; Clark, N. A.; Korblova, E.; Walba, D. M. Science 1997, 278, 1924-1927.
9. Thisayukta, J.; Nakayama, Y.; Kawauchi, S.; Takezoe, H.; Watanabe, J. J. Am. Chem. Soc. 2000, 122, 7441-7448.
10. Thisayukta, J.; Takezoe, H.; Watanabe, J. Jpn. J. Appl. Phys. 2001, 40, 3277-3287.
11. Zennyoji, M.; Takanishi, Y.; Ishikawa, K.; Thisayukta, J.; Watanabe, J.; Takezoe, H. Mol. Cryst. Liq. Cryst. 2001, 366, 693-701.
12. Sekine, T.; Niori, T.; Sone, M.; Watanabe, J.; Choi, S. W.; Takanishi, Y.; Takezoe, H. Jpn. J. Appl. Phys. 1997, 36, 6455-6463.
13. Kurosu, H.; Kawasaki, M.; Hirose, M.; Yamada, M.; Kang, S.; Thisayukta, J.; Sone, M.; Takezoe, H.; Watanabe, J. J. Phys. Chem. A 2004, 108, 4674-4678.
14. Xu, J.; Dong, R. Y.; Domenici, V.; Fodor-Csorba, K.; Veracini, A. J. Phys. Chem. B 2006, 110, 9434-9441.
15. Hough, L. E.; Clark, N. A. Phys. Rev. Lett. 2005, 95, 107802-1-4.
16. Hough, L. E.; Spannuth, M.; Nakata, M.; Coleman, D. A.; Jones, C. D.; Dantlgraber, G.; Tschierske, C.; Watanabe, J.; Korblova, E.; Walba, D. W.; Maclennan, J. E.; Glaser, M.; Clark, N. A. Science 2009, 325, 452-456.
17. Hough, L. E.; Jung, H. T.; Kruerke, D.; Heberling, M. S.; Nakata, M.; Jones, C. D.; Chen, D.; Link, D. R.; Zasadzinski, J.; Heppke, G.; Rabe, J. P.; Stocker, W.; Korblova, E.; Walba, D. W.; Glaser, M.; Clark, N. A. Science 2009, 325, 456-460.
18. Kajitani, T.; Masu, H.; Kohmoto, S.; Yamamoto, M.; Yamaguchi, K.; Kishikawa, K. J. Am. Chem. Soc. 2005, 127, 1124-1125.
19. Walba, D. M.; Korblova, E.; Huang, C. C.; Shao, R. F.; Nakata, M.; Clark, N. A. J. Am. Chem. Soc. 2006, 128, 5318-5319.
20. Choi, S.-W.; Fukuda, K.; Nakahara, S.; Kishikawa, K.; Takanishi, Y.; Ishikawa, K.; Watanabe, J.; Takezoe, H. Chem. Lett. 2006, 35, 896-897.
21. Choi, S.-W.; Kawauchi, S.; Tanaka, S.; Watanabe, J.; Takezoe, H. Chem. Lett. 2007, 36, 1018-1019.
22. Kawauchi, S.; Choi, S.-W.; Fukuda, K.; Kishikawa, K.; Watanabe, J.; Takezoe, H. Chem. Lett. 2007, 36, 750-751.
23. Yoon, D. K.; Choi, M. C.; Kim, Y. H.; Kim, M. W.; Lavrentovich, O. D.; Jung, H.-T. Nat. Mater. 2007, 6, 866-870.
24. Thisayukta, J.; Niwano, H.; Takezoe, H.; Watanabe, J. J. Mater. Chem. 2001, 11, 2717-2721.
25. Frisch, M. J.; et al. Gaussian 03, Revision C.02; Gaussian, Inc.: Pittsburgh PA, 2003.
26. Katsaras, J.; Raghunathan, V. A. Phys. Rev. Lett. 1995, 74, 2022-2025.
27. Pang, J. H.; Clark, N. A. Phys. Rev. Lett. 1994, 73, 2332-2335.
28. Miyachi, K.; Matsuyama, J.; Ishikawa, K.; Takezoe, H.; Fukuda, A. Phys. Rev. E 1995, 52, R2153-R2156.
29. Yan, F.; Hixson, C. A.; Earl, D. J. Phys. Rev. Lett. 2008, 101, 157801-1-4.