Induction and reversal of chirality of heterohelicene by charge transfer interaction in aqueous SDS micelles

Chemical Communications

Volumn , Issue 1, 2000, Pages 97-98

  Yamada, Koh ichi ^a   Kobori, Yuuki ^a   Nakagawa, Hiroko ^a  

^a JOSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIOPHENE;

ARTICLE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENERGY TRANSFER; HYDROGEN BOND; MICELLE; X RAY CRYSTALLOGRAPHY;

EID: 0034614345     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908681a     Document Type: Article

References (21)

1. D. Dieudonne, A. Gericke, C. R. Flash, X. Jiang, R. S. Farid and R. Mendelsohn, J. Am. Chem. Soc., 1998, 120, 792; J. Partyka and K. Hiltrop, Liq. Cryst., 1996, 20, 611; N. Usol'tseva, K. Praefcke, D. Singer and B. Gundogan, Liq. Cryst., 1994, 16, 617; Y. Matsumoto and R. Ueoka, Bull. Chem. Soc. Jpn., 1983, 56, 3370.
2. D. Dieudonne, A. Gericke, C. R. Flash, X. Jiang, R. S. Farid and R. Mendelsohn, J. Am. Chem. Soc., 1998, 120, 792; J. Partyka and K. Hiltrop, Liq. Cryst., 1996, 20, 611; N. Usol'tseva, K. Praefcke, D. Singer and B. Gundogan, Liq. Cryst., 1994, 16, 617; Y. Matsumoto and R. Ueoka, Bull. Chem. Soc. Jpn., 1983, 56, 3370.
3. D. Dieudonne, A. Gericke, C. R. Flash, X. Jiang, R. S. Farid and R. Mendelsohn, J. Am. Chem. Soc., 1998, 120, 792; J. Partyka and K. Hiltrop, Liq. Cryst., 1996, 20, 611; N. Usol'tseva, K. Praefcke, D. Singer and B. Gundogan, Liq. Cryst., 1994, 16, 617; Y. Matsumoto and R. Ueoka, Bull. Chem. Soc. Jpn., 1983, 56, 3370.
4. D. Dieudonne, A. Gericke, C. R. Flash, X. Jiang, R. S. Farid and R. Mendelsohn, J. Am. Chem. Soc., 1998, 120, 792; J. Partyka and K. Hiltrop, Liq. Cryst., 1996, 20, 611; N. Usol'tseva, K. Praefcke, D. Singer and B. Gundogan, Liq. Cryst., 1994, 16, 617; Y. Matsumoto and R. Ueoka, Bull. Chem. Soc. Jpn., 1983, 56, 3370.
5. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
6. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
7. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
8. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
9. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
10. P. Walde, E. Blochigner and K. Mongaki, Langmuir, 1999, 15, 2346; S. Borocci, M. Erba, G. Mancini and A. Scipioni, Langmuir, 1998, 14, 1960; D. Tickle, A. George, K. Jennings, P. Camilleri and A. J. Kirby, J. Chem. Soc., Perkin Trans. 2, 1998, 467; M. Lecouvey, C. Frochot, L. Miclo, P. Orlewski, M. Marraud, J. L. Gaillard, M. T. Cung and R. Vanderesse, Lett. Pept. Sci., 1997, 4, 359; K. Kano and T. Ishimura, J. Chem. Soc., Perkin Trans. 2, 1995, 1655; B. S. Jursic, Tetrahedron Lett., 1993, 34, 963.
11. H. Dugas, Bioorganic Chemistry: A Chemical Approach to Enzyme Action, 3rd edn., Springer-Verlag, New York, 1996.
12. H. Nakagawa, K. Yamada, H. Kawazura and H. Miyamae, Acta Crystallogr., 1984, C40, 1039.
13. K. Yamada, H. Nakagawa and H. Kawazura, Bull. Chem. Soc. Jpn., 1986, 59, 2429.
14. The symbols (P) and (M) represent 'right-handed' and 'left-handed', respectively.
15. K. Yamada, R. Ishii, H. Nakagawa and H. Kawazura, Tetrahedron: Asymmetry, 1996, 7, 737; K. Yamada, R. Ishii, H. Nakagawa and H. Kawazura, Chem. Pharm. Bull., 1997, 45, 936.
16. K. Yamada, R. Ishii, H. Nakagawa and H. Kawazura, Tetrahedron: Asymmetry, 1996, 7, 737; K. Yamada, R. Ishii, H. Nakagawa and H. Kawazura, Chem. Pharm. Bull., 1997, 45, 936.
17. H. Nakagawa, K. Gomi and K. Yamada, Enantiomer, 1998, 3, 175.
18. H. Nakagawa, K. Yamada and H. Kawazura, J. Chem. Soc., Chem. Commun., 1989, 1378.
19. -2.
20. In the continuous variations, individual components are mixed in variable ratios, but with constant total concentration. P. Job, Ann. Chim., 1928, 9, 113; J. O. Smith, D. A. Olson and A. Armitage, J. Am. Chem. Soc., 1999, 121, 2686.
21. In the continuous variations, individual components are mixed in variable ratios, but with constant total concentration. P. Job, Ann. Chim., 1928, 9, 113; J. O. Smith, D. A. Olson and A. Armitage, J. Am. Chem. Soc., 1999, 121, 2686.