An azophenol-based chromogenic pyrophosphate sensor in water

Journal of the American Chemical Society

Volumn 125, Issue 26, 2003, Pages 7752-7753

  Lee, Dong Hoon ^a   Im, Ja Hyun ^a   Son, Seung Uk ^a   Chung, Young Keun ^a   Hong, Jong In ^a,b  

^a Seoul National University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZO COMPOUND; CHROMOGENIC SUBSTRATE; PHENOL DERIVATIVE; PYROPHOSPHATE; WATER;

ARTICLE; BIOENERGY; CHEMOSENSITIVITY; COLOR; COMPLEX FORMATION; ION PAIR CHROMATOGRAPHY; SENSOR;

ANIONS; AZO COMPOUNDS; DIPHOSPHATES; HYDROGEN-ION CONCENTRATION; PHENOLS; PYRIDINES; SPECTROPHOTOMETRY; WATER;

EID: 0037528046     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja034689u     Document Type: Article

References (35)

1. (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
2. (b) Chemosensors of Ion and Molecular Recognition; Desvergne, J.-P., Czarnik, A. W., Eds.; Kluwer: Dordrecht, 1997; Vol 492.
3. (c) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646.
4. (d) Beer, P. D. Acc. Chem. Res. 1998, 31, 71-80.
5. (e) Supramolecular Chemistry for Anions; Binachi, K., Bowman-James, K., Garcia-Espana, E., Eds.; New York, 1997.
6. (f) Lehn, J.-M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
7. Limpcombe, W. N.; Sträter, N. Chem. Rev. 1996, 96, 2375-2434.
8. (a) McCarty, D. J. Arthritis Rheum. 1976, 19, 275-285
9. (b) Caswell, A.; Guilland-Cumming, D. F.; Hearn, P. R.; McGuire, M. K.; Russell, R. G. Ann. Rheum. Dis. 1983, 42 (suppl 1), 27-37.
10. (c) Doherty, M. Ann. Rheum. Dis. 1983, 42(suppl 1), 38-44.
11. (a) Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Nature. 1996, 382, 522-523.
12. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
13. (c) Lavigene, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
14. (d) Fabbrizzi, L.; Licchelli, M.; Rabioli, G.; Taglietti, A. Coord. Chem. Rev. 2000, 205, 85-108.
15. (e) Zhong, Z.; Anslyn, E. V. J. Am. Chem. Soc. 2002, 124, 9014-9015.
16. PPi sensors in aqueous solution: (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308. (c) Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925. (d) Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
17. PPi sensors in aqueous solution: (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308. (c) Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925. (d) Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
18. PPi sensors in aqueous solution: (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308. (c) Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925. (d) Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
19. PPi sensors in aqueous solution: (a) Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397-9398. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302-308. (c) Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. J. Am. Chem. Soc. 2002, 124, 3920-3925. (d) Fabbrizzi, L.; Marcotte, N.; Stomeo, F.; Taglietti, A. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
20. 3CN: (a) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464. (b) Anzenbacher, P. Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 121, 9350-9351.
21. 3CN: (a) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464. (b) Anzenbacher, P. Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 121, 9350-9351.
22. To the best of our knowledge, our system is the first colorimetric sensor for PPi in water that holds several advantages when compared to previous systems for the following reasons. Our system does not have any competing simple inorganic anions, as measured by UV-vis studies, unlike the Kikuchi system which also responds to citrate anions. Furthermore, our system operates in a wide pH range, unlike the previous systems.
23. (a) Lee, D. H.; Lee, K. H.; Hong, J.-I. Org. Lett. 2001, 3, 5-8.
24. (b) Lee, D. H.; Lee, H. Y.; Lee, K. H.; Hong, J.-I. Chem. Commun. 2001, 1189-1189.
25. (c) Lee, K. H.; Lee, H. Y.; Lee, D. H.; Hong, J.-I. Tetrahedron Lett. 2001, 42, 5447-5449.
26. (a) Suzuki, M.; Kanatomi, H.; Murase, I. Chem. Lett. 1981, 1745-1748.
27. (b) Munch, B. P.; Bradley, F. C.; Boyle, P. D.; Papaefthymiou, V.; Que, L., Jr. J. Am. Chem. Soc. 1987, 109, 7993-8003.
28. (c) Jin, S. S.; Sung, N. D.; Hynes, R. C.; Chin, J. Inorg. Chem. 1996, 35, 7472-7473.
29. (d) Torelli, S.; Belle, C.; Gautier-Luneau, I.; Pierre, J. L.; Saint-Aman, E.; Latour, J. M.; Le Page, L.; Luneau, D. Inorg. Chem. 2000, 39, 3526-3536.
30. (e) Han, M. S.; Kim, D. H. Angew. Chem., Int. Ed. 2002, 41, 3809-3811.
31. (f) Molenveld, P.; Engbersen, J. F. J.; Reinhoudt, D. N. Chem. Soc. Rev. 2000, 29, 75-86.
32. See the Supporting Information for: (a) detailed syntheses (b) pH dependence of sensor 1·2Zn.
33. Binding Constants, The Measurement of Molecular Complex Stability; Conners, K. A., Ed.; John Wiley and Sons: New York, 1987; pp 175-183.
34. (a) Although refinement of the structure has been unsatisfactory (R1 = 0.14) due to the disorder of solvents and cation molecule, it clearly shows the connectivity of the complex that we are interested in. (b) Some atoms are omitted for clarity
35. Naked eye detection for PPi is optimized under the condition of [1·2Zn] = 60 μM.