Highly Effective Fluorescent Sensor for H2PO4 -

Journal of Organic Chemistry

Volumn 69, Issue 2, 2004, Pages 581-583

  Yoon, Juyoung ^a   Kim, Sook Kyung ^a   Singh, N Jiten ^b   Lee, Jung Woo ^b   Yang, Yun Jung ^a   Chellappan, Kavitha ^b   Kim, Kwang S ^b  

^a Ewha Womans University   (South Korea)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BONDING; FLUORESCENCE; SENSORS; SYNTHESIS (CHEMICAL);

SELECTIVE BINDING;

DIMERS;

ANION; ANTHRACENE DERIVATIVE; DIMER; HYDROGEN; IMIDAZOLE DERIVATIVE; OXYGEN; PHOSPHATE;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL BINDING; CHEMOSENSITIVITY; DIMERIZATION; FLUORESCENCE; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SENSOR; SYNTHESIS;

EID: 0347132663     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035387d     Document Type: Article

References (34)

1. For recent reviews for anion receptors, see; (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486.
2. (b) Snowden, T. S.; Anslyn, E. V. Chem. Biol. 1999, 3, 740.
3. (c) Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 143.
4. (d) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
5. (e) Rudkevich, D. M.; Brzozka, Z.; Palys, M.; Visser, H. C.; Verboom, W. ; Reinhoudt, D. N. Angew. Chem., Int. Ed. 1994, 33, 467.
6. (a) Fluorescent Chemosensors for Ion and Molecular Recognition; Czarnik, A. W., Ed.; American Chemical Society: Washington, DC, 1993.
7. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302.
8. (c) Fabbrizzi, L.; Poggi, A. Chem. Soc. Rev. 1994, 197.
9. (d) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T. A.; Huxley, T. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
10. (e) Chemosensors of Ion and Molecular Recognition; Desvergne, J.-P., Czarnik, A. W., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1997.
11. Vance, D. H.; Czarnik, A. W. J. Am. Chem. Soc. 1994, 116, 9397.
12. (a) Cho, E. J.; Moon, J. W.; Ko, S. W.; Lee, J. Y.; Kim, S. K.; Yoon, J. ; Nam, K. C. J. Am. Chem. Soc. 2003, 125, 12376.
13. (b) Ojida, A.; Inoue, M.; Mito-oka, Y.; Hamachi, I. J. Am. Chem. Soc. 2003, 125, 10184.
14. (c) Ojida, A.; Mito-oka, Y.; Inoue, M.; Hamachi, I. J. Am. Chem. Soc. 2002, 124, 6256.
15. (d) Kim, S. K.; Yoon, J. Chem. Commun. 2002, 770.
16. (e) Gunnlaugsson, T.; Davis, A. P.; O'Brien, J. E.; Glynn, M. Org. Lett. 2002, 4, 2449 and references therein.
17. (f) Ojida, A.; Park, S.; Mito-oka, Y.; Hamachi, I. Tetrahedron Lett. 2002, 43, 6193.
18. (g) Wu, F.-Y.; Li, Z.; Wen, Z.-C.; Zhou, N.; Zhao, Y.-F.; Jiang, Y.-B. Org. Lett. 2002, 4, 3203.
19. (h) Causey, C. P.; Allen, W. E. J. Org. Chem. 2002, 67, 5963.
20. (i) Gunnlaugsson, T.; Davis, A. P.; Glynn, M. Chem. Commun. 2001, 2556.
21. (j) Anzenbacher, P., Jr.; Jursíková, K.; Sessler, J. L. J. Am. Chem. Soc. 2000, 122, 9350.
22. (k) Nishizawa, S.; Kaneda, H.; Uchida, T.; Teramae, N. J. Chem. Soc., Perkin Trans. 2 1998, 2325.
23. (l) Fabbrizzi, L.; Faravelli, H.; Francese, G.; Licchelli, M.; Perotti, A.; Taglietti, A. Chem. Commun. 1998, 971.
24. (m) Cooper, C. R.; Spencer, N.; James, T. D Chem. Commun. 1998, 1365.
25. (a) Kim, S. K.; Singh, N. J.; Kim, S. J.; Kim, H. G.; Kim, J. K.; Lee, J. W.; Kim, K. S.; Yoon, J. Org. Lett. 2003, 5, 2083.
26. (b) Yun, S.; Ihm, H.; Kim, H. G.; Lee, C. W.; Indrajit, B.; Oh, K. S.; Gong, Y. J.; Lee, J. W.; Yoon, J.; Lee, H. C.; Kim, K. S. J. Org. Chem. 2003, 68, 2467.
27. (c) Ihm, H.; Yun, S.; Kim, H. G.; Kim, J. K.; Kim, K. S. Org. Lett. 2002, 4, 2897.
28. (d) Sato, K.; Arai S.; Yamagishi, T. Tetrahedron Lett. 1999, 40, 5219.
29. (a) Akiyama, S.; Misumi, S.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1962, 35, 1826.
30. (b) Akiyama, S.; Misumi, S.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1962, 35, 1829.
31. (c) Akiyama, S.; Nakagawa, M. Bull. Chem. Soc. Jpn. 1971, 44, 3158.
32. Density functional calculations (B3LYP/6-31(+)G*) and self-consistent-reaction field (SCRF) calculations (solvent, acetonitrile; dielectric constant, 36.6) were carried out. Refer to refs 5a,b and: Kim, K. S. ; Tarakeshwar, P.; Lee, J. Y. Chem. Rev. 2000, 100, 4145.
33. (a) Conners, K. A. Binding Constants; Wiley: New York, 1987.
34. (b) Association constants were obtained using the computer program ENZFITTER, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, UK.