Sensing of cyanide using highly selective thiazole-based Cu2+ chemosensor

Bulletin of the Korean Chemical Society

Volumn 32, Issue , 2011, Pages 3123-3126

  Helal, Aasif ^a   Kim, Sebeom ^a   Kim, Hong Seok ^a  

^a Kyungpook National University   (South Korea)

Author keywords

Chemosensor; Copper; Cyanide; Fluorescence sensing; Thiazole

Indexed keywords

EID: 84863302644     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2011.32.8.3123     Document Type: Article

References (72)

1. (a) Cho, D.-G.; Sessler, J. L. Chem. Soc. Rev. 2009, 38, 1647.
2. (b) Caltagirone, C.; Gale, P. A. Chem. Soc. Rev. 2009, 38, 520.
3. (c) Gale, P. A.; García-Garrido, S. E.; Garric, J. Chem. Soc. Rev. 2008, 37, 151.
4. (d) Zimmermann-Dimer, L. M.; Machado, V. G. Quim. Nova 2008, 31, 2134.
5. (e) Anslyn, E. V. J. Org. Chem. 2007, 72, 687.
6. (f) Nguyen, B. T.; Anslyn, E. V. Coord. Chem. Rev. 2006, 250, 3118.
7. (g) Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Coord. Chem. Rev. 2006, 250, 3094.
8. (h) Kubik, S.; Reyheller, C.; Stüwe, S. J. Inclusion Phenom. Macrocyclic Chem. 2005, 52, 137.
9. (i) Suksai, C.; Tuntulani, T. Chem. Soc. Rev. 2003, 32, 192.
10. (j) Martínez-Mañez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
11. (a) Xu, Z.; Chen, X.; Kim, H. N.; Yoon, J. Chem. Soc. Rev. 2010, 39, 127.
12. (b) World Health Organization, Concise International Chemical Assessment Document 61, Hydrogen Cyanide and Cyanides: Human Health Aspects; Geneva, 2004; pp 4-5. http:// www.who.int/ipcs/publications/cicad/en/cicad61.pdf (accessed January 09, 2009).
13. (a) Baskin, S. I.; Brewer, T. G. In Medical Aspects of Chemical and Biological Warfare; Sidell, F., Takafuji, E. T., Franz, D. R., Eds.; TMM Publications: Washington, DC, 1997; pp 271-286. Chapter 10.
14. (b) Vennesland, B.; Comm, E. E.; Knownles, C. J.; Westly, J.; Wissing, F. Cyanide in Biology; Academic Press: London, 1981.
15. (a) Ryall, B.; Davies, J. C.; Wilson, R.; Shoemark, A.; Williams, H. D. Eur. Respir. J. 2008, 32, 740.
16. (b) Govan, J. R. W.; Deretic, V. Microbiol. Rev. 1996, 60, 539.
17. (a) The Agency for Toxic Substances and Disease Registry, Toxicological profile for cyanide, Atlanta, GA, US Department of Health and Human Services, pp 1-2, http://www.atsdr.cdc.gov/ toxprofiles/tp8-c1.pdf (accessed January 9, 2010).
18. (b) Young, C.; Tidwell, L.; Anderson, C. Cyanide: Social, Industrial, and Economic Aspects; Minerals, Metals, and Materials Society: Warrendale, 2001.
19. Mak, K. K. W.; Yanase, H.; Renneberg, R. Biosens. Bioelectron. 2005, 20, 2581.
20. (a) Xu, Z.; Pan, J.; Spring, D. R.; Cui, J.; Yoon, J. Tetrahedron 2010, 66, 1678.
21. (b) Wang, J.; Ha, C.-S. Tetrahedron 2010, 66, 1846.
22. (c) Lee, J. H.; Jeong, A. R.; Shin, I.-S.; Kim, H.-J.; Hong, J.-I. Org. Lett. 2010, 12, 764.
23. (d) Lee, G. W.; Kim, N.-K.; Jeong, K.-S. Org. Lett. 2010, 12, 2634.
24. (e) Saha, S.; Ghosh, A.; Mahato, P.; Mishra, S.; Mishra, S. K.; Suresh, E.; Das, S.; Das, A. Org. Lett. 2010, 12, 3406.
25. (f) Hong, S.-J.; Yoo, J.; Kim, S.-H.; Kim, J. S.; Yoon, J.; Lee, C.-H. Chem. Commun. 2009, 189.
26. (g) Lee, K.-S.; Lee, J. T.; Hong, J.-I.; Kim, H.-J. Chem. Lett. 2007, 36, 816.
27. (h) Chen, C.-L.; Chen, Y.-H.; Chen, C.-Y.; Sun, S.-S. Org. Lett. 2006, 8, 5053.
28. (a) Kim, Y. H.; Hong, J. I. Chem. Commun. 2002, 512.
29. (b) Anzenbacher, P. Jr.; Tyson, D. S.; Jursikova, K.; Castellano, F. N. J. Am. Chem. Soc. 2002, 124, 6232.
30. (c) Chow, C. F.; Lam, M. H. W.; Wong, W. Y. Inorg. Chem. 2004, 43, 8387.
31. (d) Badugu, R., Lakowicz, J. R.; Geddes, C. D. J. Am. Chem. Soc. 2005, 127, 3635.
32. (e) Ros-Lis, J. V.; Martinez-Manez, R.; Soto, J. Chem. Commun. 2005, 5260.
33. (f) Sun, S. S.; Lees, A. J. Chem. Commun. 2000, 1687.
34. (g) Miyaji, H.; Sessler, J. L. Angew. Chem. Int. Ed. 2001, 40, 154.
35. (h) Ganesh, V.; Sanz, M. P. C.; Mareque-Rivas, J. C. Chem. Commun. 2007, 5010.
36. (i) Zeng, Q.; Cai, P.; Li, Z.; Qin, J.; Tang, B. Z. Chem. Commun. 2008, 1094.
37. (j) Lou, X. D.; Zhang, L.; Qin, J.; Li, Z. Chem. Commun. 2008, 5848.
38. (k) Li, Z. A.; Lou, X. D.; Yu, H. B.; Li, Z.; Qin, J. Macromolecules 2008, 41, 7433.
39. (l) Chung, S. Y.; Nam, S. W.; Lim, J.; Park, S.; Yoon, J. Chem. Commun. 2009, 2866.
40. (a) Tomasulo, M.; Sortino, S.; White, A. J. P.; Raymo, F. M. J. Org. Chem. 2006, 71, 744.
41. (b) Ren, J. Q.; Zhu, W. H.; Tian, H. Talanta 2008, 75, 760.
42. (c) Garcia, F.; Garcia, J. M.; Garcia-Acosta, B.; Martinez-Manez, R.; Sancenon, F.; Soto, J. Chem. Commun. 2005, 2790.
43. (d) Ros-Lis, J. V.; Martinez-Manez, R.; Soto, J. Chem. Commun. 2002, 2248.
44. (e) Chung, Y.; Lee, H.; Ahn, K. H. J. Org. Chem. 2006, 71, 9470.
45. (f) Yang, Y. K.; Tae, J. Org. Lett. 2006, 8, 5721.
46. (g) Lee, K. S.; Kim, H. J.; Kim, G. H.; Shin, I.; Hong, J. I. Org. Lett. 2008, 10, 49.
47. (h) Kwon, S. K.; Kou, S.; Kim, H. N.; Chen, X. Q.; Wang, H.; Nam, S. W.; Kim, S. H.; Swamy, K. M. K.; Park, S.; Yoon, J. Tetrahedron Lett. 2008, 49, 4102.
48. (i) Park, S.; Kim, H. J. Chem. Commun. 2010, 9197.
49. (j) Chung, Y. M.; Raman, B.; Kim, D. S.; Ahn, K. H. Chem. Commun. 2006, 186.
50. (k) Ryu, D.; Park, E.; Kim, D. S.; Yan, S.; Lee, J. Y.; Chang, B. Y.; Ahn, K. H. J. Am. Chem. Soc. 2008, 130, 2394.
51. (l) Niu, H. T.; Jiang, X. L.; He, J. Q.; Cheng, J. P. Tetrahedron Lett. 2008, 49, 6521.
52. (m) Niu, H. T.; Su, D.; Jiang, X.; Yang, W.; Yin, Z.; He, J.; Cheng, J. P. Org. Biomol. Chem. 2008, 6, 3038.
53. (n) Ekmekci, Z.; Yilmaz, M. D.; Akkaya, E. U. Org. Lett. 2008, 10, 461.
54. Yoon, S.; Albers, A. E.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2005, 127, 16030.
55. Helal, A.; Thao, N. T. T.; Lee, S.; Kim, H.-S. J. Inclusion Phenom. Macrocyclic Chem. 2010, 66, 87.
56. Helal, A.; Kim, H.-S. Tetrahedron Lett. 2009, 50, 5510.
57. (a) Helal, A.; Lee, S. H.; Kim, S. H.; Kim, H.-S. Tetrahedron Lett. 2010, 51, 3531.
58. (b) Helal, A.; Rashid, M. H. O.; Choi, C.-H.; Kim, H.-S. Tetrahedron 2011, 67, 2794.
59. (a) Krämer, R. Angew. Chem. Int. Ed. 1998, 37, 772.
60. (b) Xiang, Y.; Tong, A.; Jin, P.; Ju, Y. Org. Lett. 2006, 8, 2863.
61. (c) Chen, X.; Li, Z.; Xiang, Y.; Tong, A. Tetrahedron Lett. 2008, 49, 4697.
62. Keck, J.; Kramer, H. E. A.; Port, H.; Hirsch, T.; Fischer, P.; Rytz, G. J. Phys. Chem. 1996, 100, 14468.
63. Henary, M. M.; Fahrni, C. J. J. Phys. Chem. A 2002, 106, 5210.
64. (a) Santra, S.; Krishnamoorthy, G.; Dogra, S. K. J. Phys. Chem. A 2000, 104, 476.
65. (b) Mosquera, M.; Penedo, J. C.; Rios Rodriguez, M. C.; Rodriguez-Prieto, F. J. Phys. Chem. 1996, 100, 5398.
66. (c) Das, K.; Sarkar, N.; Majumdar, D.; Bhattacharyya, K. Chem. Phys. Lett. 1992, 198, 443.
67. (a) Connors, K. A. Binding Constants: the Measurement of Molecular Complex Stability; New York: Wiley, 1987; pp 21-101; 339-343.
68. (b) Forgues, S. F.; LeBris, M. T.; Gutte, J. P.; Valuer, B. J. Phys. Chem. 1988, 92, 6233.
69. (c) Thordarson, P. Chem. Soc. Rev. 2011, 40, 1305.
70. Fabbrizzi, L.; Licchelli, M.; Pallavicini, P.; Parodi, L.; Taglietti, A. In Transition Metals in Supramolecuar Chemistry; Sauvage, J. P., Ed.; Fluorescent Sensors for and with Transition Metals; John Wiley & Sons Ltd: Chichester, 1999.
71. Ci, Y. X.; Zhou, T. Z. The Coordinated Complexes in Analytical Chemistry; Peking University Press: Beijing, 1984.
72. Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414.