Novel vesicular aggregates of crown-appended cholesterol derivatives which act as gelators of organic solvents and as templates for silica transcription

Journal of the American Chemical Society

Volumn 122, Issue 36, 2000, Pages 8648-8653

  Jung, Jong Hwa ^a,b   Ono, Yoshiyuki ^a   Sakurai, Kazuo ^a   Sano, Masahito ^a   Shinkai, Seiji ^a  

^a Chemotransfigiiration Project   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AZOBENZENE; CHOLESTEROL DERIVATIVE; ORGANIC SOLVENT; SILICON DIOXIDE;

ARTICLE; CIRCULAR DICHROISM; COVALENT BOND; GEL; GELATINIZATION; MOLECULAR INTERACTION; MOLECULAR SIZE; POLYMERIZATION; SPECTROSCOPY;

EID: 0034644431     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001623f     Document Type: Article

References (42)

1. (a) Esch, J. V.; Schoonbeek, F.; Loos, M. d.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Chem. Eur. J. 1999, 5, 937.
2. (b) Lu, 1.; Cocker, T. M.; Bachman, R. E.; Weiss, R. G. Langmuir 2000, 16, 20.
3. Adballah, D. J.; Weiss, R. G. Langmuir 2000, 16, 352.
4. Yoza, K.; Amanokura, N.; Ono, Y.; Akao, T.; Shinmori, H.; Takeuchi, M.; Shinkai, S.; Reinhoudt, D. N. Chem. Eur. J. 1999, 5, 2722.
5. (a) Vries, E. J. de.; Kellogg, R. M. J. Chem. Soc., Client. Commun. 1993, 238.
6. (b) Loos, M. de; Esch, J. van; Stokroos, I.; Kellogg, R. M.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 12675.
7. (a) Wang, R.; Geiger, C.; Chen, L.; Swanson, B.; Whittem, D. G. J Am. Chem. Soc. 2000, 122, 2399.
8. (b) Geiger, C.; Stanesch, M.; Chen, L. H.; Whittem, D. G. Langmuir 1999, 75, 5. 2241.
9. (a) Hanabusa, K.; Okui, K.; Karaki, K.; Koyama, T.; Shirai, H. J. Chem. Soc. Chem. Commun. 1992, 1371.
10. (b) Hanabusa, K.; Kawakami, K.; Kimura, M.; Shirai, H. Chem. Lett. 1997, 191 and references therein.
11. Sohna, J.-E. S.; Pages, F. Chem. Commun. 1997, 327.
12. (a) Otsuni, E:; Kamaras, P.; Weiss, R. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1324 and references therein,
13. (b) Terech, P.; Furman, I.; Weiss, R. G. J. Phys. Chem. 1995, 99, 9558 and references therein.
14. (a) Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.; Komori, T.; Ohseto, F.; Ueda, K.; Shinkai, S. J. Am. Chem. Soc. 1994, 116, 6664 and references therein,
15. (b) James, T. D.; Murata, K.; Harada, T.; Ueda, K.; Shinkai, S. Chem. Lett. 1994, 273.
16. Jeong, S. W.; Murata, K.; Shinkai, S. Supramol. Sei. 1996, 3, 83.
17. Brotin, T.; Utermöhlen, R.; Pages, F.; Bouas-Laurent, H.; Desvergne, J.-P. J. Chem. Soc., Chem. Commun. 1991, 416.
18. (a) For recent comprehensive reviews, see Terech, P.; Weiss, R. G. Chem. Reif. 1997, 97, 3133.
19. (b) Shinkai, S.; Murata, K. J. Mater. Client. (Feature Article) 1998, 8, 485.
20. (a) Jung, J. H.; Ono, Y.; Shinkai, S. Langmuir 2000, 16, 1643.
21. (b) Jung, J. H.; Ono, Y.; Shinkai, S. J. Chem. Soc., Perkin Trans 2 1999, 1289.
22. Ono, Y.; Nakashima, K.; Sano, M.; Kanekiyo, Y.; Inoue, K.; Hojo, J.; Shinkai, S. Chem. Commun. 1998, 7477.
23. Ono, Y.; Kanekiyo, Y.; Inoue, K.; Hojo, J.; Shinkai, S. Chem. Lett. 1999, 23.
24. (e) Ono Y.; Nakashima, K.; Sano, M.; Hojo, J.; Shinkai, S. Chem. Lett. 1999, 1119.
25. (a) Echegoyen, L. E.; Hemandez, J.; Kaifer, A. E.; Gokel, G. W.; Echegoyen, L. J. Chem. Soc. Chem. Commun. 1988, 836.
26. (b) Nakano, A.; Hemadez, J. C.; Dewall, S. L.; Wang, K.; Berger. D. R.; Gokel, G. W. Supramol. Sei. 1997, 8, 21.
27. Echegoyen. L. E.; Portugal, L.; Miller, S. R.; Hemandez, J. C.; Echegoyen, L.; Gokel, G. W. Tetrahedron Lett. 1988, 29, 4065.
28. Okahara, M.; Kuo, P. L.; Yamamura, S.; Ikeda, I. J. Chem. Soc. Chem. Commun. 1980, 586.
29. (a) Schacht, S.; Huo, Q.; Voigt-Martin, I. G.; Stucky, G. D.; Schüth, F. Science 1996, 273, 768.
30. (b) Huo, Q.; Fena, J.; Schüth, F.; Stucky, G. D. Chem. Mater. 1997,14, 119.
31. Caruso, F. Chem. Eur. J. 2000, 6. 413.
32. Caruso, F.; Caruso, R. A.; Möhwald, H. Science 1998, 282, 1111.
33. (a) Tanev, P. T.; Ling, Y.; Pinnavaia, J. Am. Chem. Soc. 1997,119, 8616.
34. (b) Kirn, S. S.; Zhang, W.; Pinnavaia, T. J. Science 1998,282, 1302.
35. The xerogel more suitable to the SEM observation was obtained from cyclohexane solution (mp: 6.47 °C) than from a 1-butanol solution (mp: -90 °C), because this was prepared by a freezing-and-pumping method. The structure of xerogel does not depended on organic solvent according to ref II.
36. (a) Kunitake, T. Angew. Chem., Int. Ed. Engl. 1992, 21, 709.
37. (b) Kunitake, T.; Ishikawa, Y.; Shimoumura, M. J. Am. Chem. Soc.1986, 108, 327.
38. Fuhrhop, J.-H.; Köning, J. Membranes and Molecular Assemblies: Tlie Synkinetic Approach; The Royal Society of Chemistry: 1994.
39. In fact, we have already measured XRD. The peak which deserves publication was not observed, however. Judging from the TEM pictures, the space between silica layers is about 5 nm. One should note that this is the averaged value and there is a significant distribution in the spacing. We thus consider that this distribution is the reason we could not observed the peak in XRD. The many reproducible TEM pictures support, however, that there exist a clear space between the silica.
40. (a) Mehnert, C. P.; Weaver, D. W.; Ying, J. Y. J. Am. Client. Soc. 1998, 120, 12289.
41. (b) Mehnert, C. P.; Ying, J. Y. Chem. Com,. 1997, 2215.
42. Chemical component of Pd was confirmed by Electron Spectroscopy for Chemical Analysis (ESCA): it consists of Pd(0) and Pd(II) derivative.