Sugar-integrated gelators of organic solvents - Their remarkable diversity in gelation ability and aggregate structure

Chemistry - A European Journal

Volumn 5, Issue 9, 1999, Pages 2722-2729

  Yoza, Kenji ^a   Amanokura, Natsuki ^a   Ono, Yoshiyuki ^a   Akao, Tetsuyuki ^b   Shinmori, Hideyuki ^c   Takeuchi, Masayuki ^c   Shinkai, Seiji ^a   Reinhoudt, David N ^d  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b FUKUOKA INDUSTRIAL TECHNOLOGY CENTER   (Japan)

^c KYUSHU UNIVERSITY   (Japan)

^d UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

Hydrogen bonds; Molecular assembly; Organic gels; Saccharides; Sol gel processes; Sugars; Supramolecular chemistry

Indexed keywords

CARBOHYDRATE; GALACTOSE; SOLVENT;

ARTICLE; CHEMICAL ANALYSIS; CHIRALITY; HYDROGEN BOND; INFRARED SPECTROMETRY; PROTEIN ANALYSIS; PROTEIN ASSEMBLY; PROTEIN FAMILY; PROTEIN STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0032844074     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(19990903)5:9<2722::AID-CHEM2722>3.0.CO;2-N     Document Type: Article

References (38)

1. a) K. Hanabusa, K. Okui, T. Koyama, H. Shirai, J. Chem. Soc. Chem. Commun. 1992, 1371, and references therein;
2. b) K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem. 1996, 108, 2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1949;
3. b) K. Hanabusa, M. Yamada, M. Kimura, H. Shirai, Angew. Chem. 1996, 108, 2086; Angew. Chem. Int. Ed. Engl. 1996, 35, 1949;
4. c) K. Hanabusa, K. Shimura, K. Hirose, M. Kimura, H. Shirai, Chem. Lett. 1996, 885;
5. d) K. Hanabusa, A. Kawakami, M. Kimura, H. Shirai, Chem. Lett. 1997, 191;
6. e) T. Kato, G. Kondo, K. Hanabusa, Chem. Lett. 1998, 193;
7. f) Y. Hishikawa, K. Sada, R. Watanabe, M. Miyata, K. Hanabusa, Chem. Lett. 1998, 795.
8. E. J. de Vries, R. M. Kellogg, J. Chem. Soc. Chem. Commun. 1993, 238.
9. M. Takafuki, H. Ihara, C. Hirayama, H. Hachisako, K. Yamada, Liq. Cryst. 1995, 18, 97.
10. J.-E. S. Sobna, F. Fages, Chem. Commun. 1997, 327.
11. a) E. Otsuni, P. Kamaras, R. G. Weiss, Angew. Chem. 1996, 108, 1423; Angew. Chem. Int. Ed. Engl. 1996, 35, 1324, and references therein;
12. a) E. Otsuni, P. Kamaras, R. G. Weiss, Angew. Chem. 1996, 108, 1423; Angew. Chem. Int. Ed. Engl. 1996, 35, 1324, and references therein;
13. b) P. Terech, R. G. Weiss, Chem. Rev. 1997, 97, 3133;
14. c) Y-C. Lin, B. Kachar, R. G. Weiss, J. Am. Chem. Soc. 1989, 111, 5542;
15. d) I. Furman, R. G. Weiss, Langmuir 1993, 9, 2084;
16. e) L. Lu, R. G. Weiss, Langmuir 1995, 11, 3630;
17. f) L. Lu, R. G. Weiss, Chem. Commun. 1996, 2029.
18. a) P. Terech, I. Fuman, R. G. Weiss, J. Phys. Chem. 1995, 99, 9558, and references therein;
19. b) P. Terech, J. J. Allegraud, C. M. Garner, Langmuir 1998, 14, 3991.
20. K. Murata, M. Aoki, T. Suzuki, T. Kanada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda, S. Shinkai, J. Am. Chem. Soc. 1994, 116, 6664, and references therein.
21. T. D. James, K. Murata, T. Kanada, K. Ueda, S. Shinkai, Chem. Lett. 1994, 273.
22. S. W. Jeong, K. Murata, S. Shinkai, Supramol. Sci. 1996, 3, 83.
23. T. Brotin, R. Utermolen, F. Fagles, H. Bouas-Laurent, J.-P. Desvergne, J. Chem. Soc. Chem. Commun. 1991, 416.
24. a) J. van Esch, S. de Feyter, R. M. Kellogg, F. de Schryver, B. L. Feringa, Chem. Eur. J. 1997, 3, 1238;
25. b) R. Oda, I. Huc, S. J. Candau, Angew. Chem. 1998, 110, 2835; Angew. Chem. Int. Ed. 1998, 37, 2689.
26. b) R. Oda, I. Huc, S. J. Candau, Angew. Chem. 1998, 110, 2835; Angew. Chem. Int. Ed. 1998, 37, 2689.
27. S. Yamasaki, H. Tsutsumi, Bull. Chem. Soc. Jpn. 1996, 69, 561, and references therein.
28. K. Yoza, Y. Ono, K. Yoshihara, T. Akao, H. Shinmori, M. Takeuchi, S. Shinkai, D. N. Reinhoudt, Chem. Commun. 1998, 907.
29. M. Svaan, T. Anthonsen, Acta. Chem. Scand. Ser. B 1986, 40, 119.
30. The following solvents were also tested: m-cresol, tetrahydrofuran, dioxane, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfoxide, 1-methyl-2-pyrrolidone, methanol, benzyl alcohol, acetic acid, n-propylamine, diethylamine, aniline, pyridine, and 2,2,2-trifluoroethanol, but all the five gelators were too soluble in these solvents and gels were not formed.
31. The same idea was also proposed by Weiss et al. on the basis of the spectroscopic data in Ref. [5] and R. Mukkamala, R. G. Weiss, J. Chem. Soc. Chem. Commun. 1995, 375.
32. A similar correlation between the ΔΗ and the gelator solubility was found in a related system. See N. Amanokura, K. Yoza, H. Shinmori, S. Shinkai, D. N. Reinhoudt, J. Chem. Soc. Perkin Trans. 2 1998, 2585.
33. [31] the explanation of this figure (plots of R against gelator concentration) is partially confused.
34. M. Aoki, K. Nakashima, H. Kawabata, S. Tsutsui, S. Shinkai, J. Chem. Soc. Perkin Trans. 2 1993, 347.
35. N. Inamoto, Hamme Rule, Maruzen, Tokyo, 1983, p. 90.
36. K. Araki, K. Iwamoto, S. Shinkai, T. Matsuda, Bull. Chem. Soc. Jpn. 1990, 63, 3480.
37. For the preparation of dry samples for SEM observations, see ref. [7] and S. W. Jeong, S. Shinkai, Nanotechnology 1997, 8, 179.
38. -1 respectively).