An effective fluorescent chemosensor for mercury ions [3]

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6769-6770

  Prodi, Luca ^a   Bargossi, Carlotta ^a   Montalti, Marco ^a   Zaccheroni, Nelsi ^a   Su, Ning ^b   Bradshaw, Jerald S ^b   Izatt, Reed M ^b   Savage, Paul B ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MERCURY;

CHEMOSENSITIVITY; DIAGNOSTIC VALUE; FLUORESCENCE; LETTER; LIGAND BINDING; LUMINESCENCE; METAL BINDING; PHOTOCHEMISTRY; PHYSICAL CHEMISTRY; SENSOR;

EID: 0034686693     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0006292     Document Type: Letter

References (28)

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10. For example see: (a) Bartsch, R. A.; Chapoteau, E.; Czech, B. P.; Krzykawski, J.; Kamar, A.; Robison, T. W. J. Org. Chem. 1994, 59, 616. (b) Zazula, W.; Chapoteau, E.; Czech, B. P.; Kumar, A. J. Org. Chem. 1992, 57, 6720. (c) Fery-Forgues, S.; Bourson, S.; Dallery, L.; Valeur B. New J. Chem. 1990, 14, 617.
11. For example see: (a) Bartsch, R. A.; Chapoteau, E.; Czech, B. P.; Krzykawski, J.; Kamar, A.; Robison, T. W. J. Org. Chem. 1994, 59, 616. (b) Zazula, W.; Chapoteau, E.; Czech, B. P.; Kumar, A. J. Org. Chem. 1992, 57, 6720. (c) Fery-Forgues, S.; Bourson, S.; Dallery, L.; Valeur B. New J. Chem. 1990, 14, 617.
12. (a) Su, N.; Bradshaw, J. S.; Zhang, X. X.; Song, H.-C.; Savage, P. B.; Xue, G.-P.; Krakowiak, K. E.; Izatt, R. M. J. Org. Chem. 1999, 64, 8855.
13. (b) Su, N.; Bradshaw, J. S.; Savage, P. B.; Krakowiak, K. E.; Izatt, R. M.; DeWall, S. L.; Gokel G. W. Tetrahedron 1999, 55, 9737.
14. (c) Su, N.; Bradshaw, J. S.; Savage, P. B.; Krakowiak, K. E.; Izatt, R. M. J. Org. Chem. 1999, 64, 3825.
15. (d) Yang, Z.; Bradshaw, J. S.; Zhang, X. X.; Savage, P. B.; Krakowiak, K. E.; Dalley, N. K.; Su, N.; Bronson, T.; Izatt. R. M. J. Org. Chem. 1999, 64, 3162.
16. (e) Su, N.; Bradshaw, J. S.; Savage, P. B.; Krakowiak, K. E.; Izatt, R. M. J. Heterocycl. Chem. 1999, 36, 771.
17. (f) Bordunov, A. V.; Bradshaw, J. S.; Pastushok, V. N.; Zhang, X. X.; Kou, X.; Dalley, N. K.; Yang, Z.; Savage, P. B.; Izatt, R M. Tetrahedron 1997, 53, 17595.
18. Prodi, L.; Bolletta, F.; Montalti, M.; Zaccheroni, N.; Savage, P. B.; Bradshaw, J. S.; Izatt, R. M. Tetrahedron Lett. 1998, 39, 5451.
19. Yoon, J., Ohler, N. E.; Vance, D. H.; Aumiller, W. D.; Czarnik, A. W. Tetrahedron Lett. 1997, 38, 3845.
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22. a values of 2.5 and 6.4 for the nitrogen and the phenolic group, respectively (Klofutar, C.; Paljk, S.; Krasovec, F.; Horvat, I. Mikrochim. Acta 1973, 559)), particularly if the different solvent and potential hydrogen bonding interactions with the macrocycle are considered.
23. -5 M. The behavior of 2 in the presence of metal cations was measured in methanol - water (1:1 v/v) to avoid working near the solubility limit and possible aggregation concentration of 2. Nevertheless, the ion selectivities of 2 are expected to be the same in water as they are in the mixed aqueous solvent system (for an example of ion selectivities of macrocycles in methanol-water mixtures compared to selectivities in water see: Zhang, X. X.; Izatt, R. M.; Krakowiak, K. E.; Bradshaw, J. S. Inorg. Chim. Acta 1997, 254, 43).
24. 2+ are included in the Supporting Information.
25. Winkler, J. D.; Bowen C. M.; Michelet, V. J. Am. Chem. Soc. 1998, 120, 3237.
26. For additional recent examples, see: (a) Alfimov, M. V.; Gromov, S. P.; Fedorov, Y. V.; Fedorova, O. A.; Vedemikov, A. I.; Churakov, A. V.; Kuz'mina, L. G.; Howard, J. A. K.; Bossmann, B.; Braun, A.; Woerner, M.; Sears, D. F.; Saltiel, J. J. Am. Chem. Soc. 1999, 727, 4992. (b) Beall, S. L.; Mani, N. S.; White, A. J. P.; Williams, D. J.; Marrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1998, 63, 5806. (c) Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951.
27. For additional recent examples, see: (a) Alfimov, M. V.; Gromov, S. P.; Fedorov, Y. V.; Fedorova, O. A.; Vedemikov, A. I.; Churakov, A. V.; Kuz'mina, L. G.; Howard, J. A. K.; Bossmann, B.; Braun, A.; Woerner, M.; Sears, D. F.; Saltiel, J. J. Am. Chem. Soc. 1999, 727, 4992. (b) Beall, S. L.; Mani, N. S.; White, A. J. P.; Williams, D. J.; Marrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1998, 63, 5806. (c) Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951.
28. For additional recent examples, see: (a) Alfimov, M. V.; Gromov, S. P.; Fedorov, Y. V.; Fedorova, O. A.; Vedemikov, A. I.; Churakov, A. V.; Kuz'mina, L. G.; Howard, J. A. K.; Bossmann, B.; Braun, A.; Woerner, M.; Sears, D. F.; Saltiel, J. J. Am. Chem. Soc. 1999, 727, 4992. (b) Beall, S. L.; Mani, N. S.; White, A. J. P.; Williams, D. J.; Marrett, A. G. M.; Hoffman, B. M. J. Org. Chem. 1998, 63, 5806. (c) Unob, F.; Asfari, Z.; Vicens, J. Tetrahedron Lett. 1998, 39, 2951.