Dipyrrole carboxamide derived selective ratiometric probes for cyanide ion

Organic Letters

Volumn 8, Issue 22, 2006, Pages 5053-5056

  Chen, Chun Lin ^a,b   Chen, Yen Hsiu ^a   Chen, Chan Yu ^a,c   Sun, Shih Sheng ^a  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL CHUNG CHENG UNIVERSITY   (Taiwan)

^c NATIONAL CENTRAL UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33750912766     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061969g     Document Type: Article

References (39)

1. (a) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
2. (b) Amendola, V.; Esteban-Gómez, D.; Fabbrizzi, L.; Licchelli, M. Acc. Chem. Res. 2006, 39, 343-353.
3. (a) Kulig, K. W. Cyanide Toxicity; U.S. Department of Health and Human Services: Atlanta, GA, 1991.
4. (b) Baskin, S. I.; Brewer, T. G. In Medical Aspects of Chemical and Biological Warfare; Sidell, F. R., Takafuji, E. T., Franz, D. R., Eds.; TMM Publications: Washington, DC, 1997; pp 271-286.
5. (c) Baird, C.; Cann, M. Environmental Chemistry; Freeman: New York, 2005.
6. Miller, G. C.; Pritsos, C. A. Cyanide: Soc., Ind. Econ. Aspects, Proc. Symp. Annu. Meet. TMS 2001, 73-81.
7. (a) Chung, Y. M.; Raman, B.; Kim, D.-S.; Ahn, K. H. Chem. Commun. 2006, 186-188.
8. (b) Tomasulo, M.; Sortino, S.; White, A. J. P.; Raymo, F. M. J. Org. Chem. 2006, 71, 744-753.
9. (c) Tomasolu, M.; Raymo, F. M. Org. Lett. 2005, 7, 4633-4636.
10. (d) Chow, C.-F.; Lam, M. H. W.; Wong, W.-Y. Inorg. Chem. 2004, 43, 8387-8393.
11. (e) Felscher, D.; Wulfmeyer, M. J. Anal. Toxicol. 1998, 22, 363-366.
12. (f) Ros-Lis, J. V.; Martínez-Máñez, R.; Soto, J. Chem. Commun. 2002, 2248-2249.
13. (g) Ajayaghosh, A. Acc. Chem. Res. 2005, 38, 449-459.
14. (a) Martinez-Manez, R.; Sancenon, F. Chem. Rev. 2003, 103, 4419-4476 and references therein.
15. (b) Brooks, S. J.; Gale, P. A.; Light, M. E. Chem. Commun. 2005, 4696-4698.
16. (c) Brooks, S. J.; Edwards, P. R.; Gale, P. A.; Light, M. E. New J. Chem. 2006, 30, 65-70.
17. (d) Wu, C.-Y.; Chen, M.-S.; Lin, C.-A.; Lin, S.-C.; Sun, S.-S. Chem. Eur. J. 2006, 12, 2263-2269.
18. Ajayaghosh, A.; Carol, P.; Sreejith, S. J. Am. Chem. Soc. 2005, 127, 14962-14963.
19. (a) Peng, X.; Wu, Y.; Fan, J.; Tian, M.; Han, K. J. Org. Chem. 2005, 70, 10524-10531.
20. (b) Liu, B.; Tian, H. J. Mater. Chem. 2005, 15, 2681-2686.
21. (c) Wen, Z. C.; Jiang, Y. B. Tetrahedron 2004, 60, 11109-11115.
22. (d) Kubo, Y.; Yamamoto, M.; Ikeda, M.; Takeuchi, M.; Shinkai, S.; Yamaguchi, S.; Tamao, K. Angew. Chem., Int. Ed. 2003, 42, 2036-2040.
23. (e) Yann, B.; Martin, J. C.; David, P.; Rachel, S. Chem. Commun. 2002, 1930-1931.
24. (f) Nishizawa, S.; Kato, Y.; Teramae, N. J. Am. Chem. Soc. 1999, 121, 9463-9464.
25. Cheng and coworkers reported a dipyrrole-2-carboxamide-phenylene compound that exhibited weak binding affinity to fluoride in DMSO solution. Yin, Z.; Li, Z.; Yu, A.; He, J.; Cheng, J.-P. Tetrahedron Lett. 2004, 45, 6803-6806.
26. Connors, K. A. Binding Constants; John Wiley and Sons: New York, 1987.
27. (a) SPECFIT, version 3.0; Spectra Software Associates.
28. (b) Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1985, 32, 95-101.
29. (c) Gampp, H.; Maeder, M.; Meyer, C. J.; Zuberbühler, A. D. Talanta 1986, 33, 943-951.
30. Compound 2 started to precipitate when water content was over 50%.
31. (a) Badugu, R.; Lakowicz, J. R.; Geddes, C. D. J. Am. Chem. Soc. 2005, 127, 3635-3641.
32. (b) Sun, S.-S.; Lees, A. J.; Zavalij, P. Y. Inorg. Chem. 2003, 42, 3445-3453.
33. (c) Anzenbacher, P., Jr.; Tyson, D. S.; Jursiková, K.; Castellano, F. N. J. Am. Chem. Soc. 2002, 124, 6232-6233.
34. (d) Miyaji, H.; Sessler, J. L. Angew. Chem., Int. Ed. 2001, 40, 154-157.
35. Compound 1 also displays high selectivity of cyanide over other common inorganic anions. See the Supporting Information for the fluorescence response of 1 in the presence of 10 equiv of selected anions.
36. Kim, Y. K.; Lee, Y.-H.; Lee, H-Y.; Kim, M. K.; Cha, G. S.; Ahn, K. H. Org. Lett. 2003, 5, 4003-4006.
37. Boiocchi, M.; Del Boca, L.; Esteban-Gómez, D.; Fabbrizzi, L.; Lucchelli, M.; Monzani, E. Chem. Eur. J. 2005, 11, 3097-3104.
38. -. The ability to protonate the cyanide adduct by these three anions and turn the solution back to colorless is consistent with the final process depicted in Scheme 2.
39. 13C NMR spectrum of the cyanide adduct was unsuccessful due to the very low solubility of 1.