An azophenol-based chromogenic anion sensor

Organic Letters

Volumn 3, Issue 1, 2001, Pages 5-7

  Lee, Dong Hoon ^a   Lee, Kwan Hee ^a   Hong, Jong In ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0003148193     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006690t     Document Type: Article

References (32)

1. (a) Takagi, M. In Cation Binding by Macrocvcles; Inoue, Y., Gokel, W. G., Ed.; Marcel Dekker: New York, 1990; Chapter 11,pp 465-496.
2. (b) Topics in Current Chemistry (Supramolecular Chemistry I); Weber, E., Ed.; Springer: Berlin, 1993; Vol. 165.
3. (c) Löhr, H.-G.; Vögtle, F. Acc. Chem. Res. 1985, 18, 65-72.
4. (d) Hayashita, T.; Takagi, M. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Suslick, K. S., Eds.; Pergamon: Oxford, 1996; pp 635-669.
5. (a) Brzózka, Z. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Suslick, K. S., Eds.; Pergamon: Oxford, 1996; pp 187-212.
6. (b) Chemosensors of Ion and Molecular recognition; Desvergne, J.-P., Czarnik, A. W., Eds.; Kluwer: Dordrecht, 1997; Vol. 492.
7. (c) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
8. (d) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649-652.
9. (e) Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Nature. 1996, 382, 522-523.
10. (a) Lavigene, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
11. (b) Gale, P. A.; Twyman, L. J.; Handlin, C. I.; Sessler, J. L. Chem. Commun. 1999, 1851-1852.
12. (a) Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438-10439.
13. (b) Miyaji, H.; Sato, W; Sessler, J. L. Angew. Chem. Int. Ed. 2000, 39, 1777-1780.
14. (c) Anzenbacher, P., Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350-9351.
15. For reviews, see: (a) Supramolecular Chemistry of unions; Blanchi, A., Bowman-James, K., Garcia-Espana, E., Eds.; Wilely-VCH: New York, 1997.
16. (b) Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
17. (c) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
18. (a) Xie, H.; Yi, S.; Wu, S. Chem. Commun. 1999, 2751-2754.
19. (b) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325.
20. (c) Kubo, Y.; Tsukahara, M; Ishihara, S.; Tokita, S. Chem. Commun. 2000, 653-654.
21. (d) Hayashita, T.; Onodera, T.; Kato, R.; Nishizawa, S.; Teramae, N. Chem. Commun. 2000, 755-756.
22. Tsuge A.; Moriguchi, T.; Mataka, S.; Tachiro, M. J. Chem. Soc. Perkin Trans. 1993, 2211.
23. Muche, M.-S.; Göbel, M. W. Angew. Chem., Int. Ed. Engl. 1996, 35, 2126-2129.
24. (a) Taub, B.; Hino, J. B. J. Org. Chem. 1961, 26, 5238-5239.
25. (b) Nishizawa, S.; Bühlmann, P.; Iwao, M.; Umezawa, Y. Tetrahedron Lett. 1995, 36, 6483.
26. Wilcox, C. S. In Frontiers in Supramolecular Chemistry; Schneider, H.-J., Dürr, H., Eds.; Verlag Chemie: WeinHeim, 1991; p 165.
27. Kelly, T. R.; Kim, M. H. J. Am. Chem. Soc. 1994, 116, 7072-7080.
28. Binding Constants, The Measurement of Molecular Complex Stability; Conners, K. A., Ed.; John Wiley and Sons: New York, 1987; pp 24-28.
29. - do, from light yellow to red.
30. Nishizawa, S.; Kato, R.; Hayashita, T.; Teramae, N. Anal. Sci. 1998, 14, 595-597.
31. -. For details, see the Supporting Information.
32. Azophenol 3 shows a dramatic color change from yellow to blue in the presence of fluoride anion. This result will be published elsewhere.