A coordination gelator that shows a reversible chromatic change and sol-gel phase-transition behavior upon oxidative/reductive stimuli

Journal of the American Chemical Society

Volumn 126, Issue 28, 2004, Pages 8592-8593

  Kawano, Shin Ichiro ^a   Fujita, Norifumi ^a   Shinkai, Seiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER DERIVATIVE;

ARTICLE; DEVICE; DIPOLE; ELECTROCHEMICAL ANALYSIS; HYDROGEN BOND; MOLECULAR WEIGHT; OXIDATION; PHASE TRANSITION; REACTION ANALYSIS; REDUCTION; ROOM TEMPERATURE;

EID: 3242684963     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja048943+     Document Type: Article

References (30)

1. McQuade, D. T.; Pullen, A. E.; Swager, T. M. Chem. Rev. 2000, 100, 2537-2574.
2. Osada, Y.; Okuzaki, H.; Hori, H. Nature 1992, 355, 242-244.
3. (a) Balzani, V.; Credi, A.; Raymo, F. M.; Stoddart, J. F. Angew. Chem., Int. Ed. 2000, 39, 3348-3391.
4. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515-1566.
5. For recent reviews, see: (a) Terech, P.; Weiss, R. G. Chem. Rev. 1997, 97, 3133-3159.
6. (b) van Esch, J. H.; Feringa, B. L. Angew. Chem., Int. Ed. 2000, 39, 2263-2266.
7. (c) Gronwald, O.; Shinkai, S. Chem. Eur. J. 2001, 7, 4328-4334.
8. Murata, K.; Aoki, M.; Suzuki, T.; Harada, T.; Kawabata, H.; Komori, T.; Ohseto, F.; Ueda, K.; Shinkai, S. J. Am. Chem. Soc. 1994, 116. 6664-6676.
9. Hanabusa, K.; Yamada, Y.; Kimura, M.; Shirai, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1949-1951.
10. van Esch, J.; Schoonbeek, F.; de Loos, M.; Kooijman, H.; Spek, A. L.; Kellogg, R. M.; Feringa, B. L. Chem. Eur. J. 1999, 5, 937-950.
11. Yoza, K.; Amanokura, N.; Ono, Y.; Akao, T.; Shinmori, H.; Takeuchi, M.; Shinkai, S.; Reinhoudt, D. N. Chem. Eur. J. 1999, 5, 2722-2729.
12. Kobayashi, H.; Amaike, M.; Jung, J. H.; Friggeri, A.; Shinkai, S.; Reinhoudt, D. N. Chem. Commun. 2001, 1038-1039.
13. Ishi-i, T.; Ono, Y.; Shinkai, S. Chem. Lett. 2000, 808-809.
14. (a) Sugiyasu, K.; Fujita, N.; Takeuchi, M.; Yamada, S.; Shinkai, S. Org. Biomol. Chem. 2003, 1, 895-899.
15. (b) Sugiyasu, K.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2004, 43, 1229-1233.
16. (a) Beck, J. B.; Roman, S. J. J. Am. Chem. Soc. 2003, 125, 13922-13923.
17. (b) Sohna, J.-R. S.; Fages, F. Chem. Commun. 1997, 327-328.
18. (c) Kawano, S.-i.; Fujita, N.; van Bommel, K. J. C.; Shinkai, S. Chem. Lett. 2003, 32, 12-13.
19. (d) Kuroiwa, K.; Shibata, T.; Takada, A.; Nemoto, N.; Kimizuka, N. J. Am. Chem. Soc. 2004, 126, 2016-2021.
20. Williams, R. M.; Cola, L. D.; Hartl, F.; Lagref, J.-J.; Planeix, J.-M.; Cian, A. D. Hosseini, M. W. Coord. Chem. Rev. 1997, 230, 253-261.
21. Livoreil, A.; Sauvage, J.-P.; Armaroli, N.; Balzani, V.; Flamigni, L.; Ventura, B. J. Am. Chem. Soc. 1997, 119, 12114-12124.
22. See Supporting Information.
23. 2 complex are EPR silent, which means that Cu(II) ion does not contribute to this chromatic change.
24. (a) Ichinaga, A. K.; Kirchhoff, J. R.; McMillin, D. R.; Dietrich-Buchecker, C. O.; Marnot, P. A.; Sauvage, J.-P. Inorg. Chem. 1987, 26, 4290-4292.
25. (b) Phifer, C. C.; McMillin, D. R. Inorg. Chem. 1986, 25, 1329-1333.
26. (c) Burke, P. J.; Henrick, K.; McMillin, D. R. Inorg. Chem. 1982, 21, 1881-1886.
27. Zarges, W.; Hall, J.; Lehn, J.-M. Helv. Chim. Acta 1994, 74, 1843-1852.
28. Over the molar ratio [Cu(I)]/[1] = 0.5, the gel stability was weakened because the 1:2 complex was not the main species, which was monitored by the relative decrease in the MLCT band intensity.
29. It is rare that the aggregate of cholesteryl derivative with the (S)-configuration at C-3 shows these left-handed helical structures. Although we herein could not reveal why this anti-motif was observed, the details of the assembled architecture are being investigated.
30. 2 complexes were evidenced by UV and EPR spectra; see Supporting Information.