Design of a semirigid molecule as a selective fluorescent chemosensor for recognition of Cd(II)

Organic Letters

Volumn 10, Issue 17, 2008, Pages 3653-3656

  Tang, Xiao Liang ^a   Peng, Xiao Hong ^a   Dou, Wei ^a   Mao, Jie ^a   Zheng, Jiang Rong ^a   Qin, Wen Wu ^a   Liu, Wei Sheng ^a,b   Chang, Jin ^a   Yao, Xiao Jun ^a  

^a LANZHOU UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

8 QUINOLINOL; CADMIUM; DIVALENT CATION; DRUG DERIVATIVE; FLUORESCENT DYE; OXADIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; METHODOLOGY; SPECTROFLUOROMETRY; SYNTHESIS; THERMODYNAMICS;

CADMIUM; CATIONS, DIVALENT; FLUORESCENT DYES; MODELS, MOLECULAR; OXADIAZOLES; OXYQUINOLINE; SPECTROMETRY, FLUORESCENCE; THERMODYNAMICS;

EID: 55949126718     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801382f     Document Type: Article

References (47)

1. (a) Schraderr, T.; Hamilton, A. D., Eds. Functional Synthetic Receptors; Wiley-VCH: Weinheim, Germany, 2005.
2. (b) Desvergne, J. P.; Czarnik, A. W. Chemosensors of Ion and Molecule Recognition; Kluwer: Dordrecht, 1997.
3. (c) Fluorescent Chemosensors for Ion and Molecule Recognition; Czarnik, A. W., Ed.; American Chemical Society: Washington, DC, 1992.
4. (d) Martínez-Máñez, R.; Sancenón, F. Chem. Rev. 2003, 103, 44.
5. (e) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486-516.
6. (f) de Silva, A. P.; Gunaratne, H.Q. N.; Gunnlaugsson, T.; Huxley, A. J. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Chem. Rev. 1997, 97, 1515.
7. For reviews, see: (a) Amendola, V.; Fabbrizzi, L.; Forti, F.; Licchelli, M.; Mangano, C.; Pallavicini, P.; Poggi, A.; Sacchi, D.; Taglieti, A. Coord. Chem. Rev. 2006, 250, 273.
8. (b) Rurack, K.; Resch-Genger, U. Chem. Soc. Rev. 2002, 116.
9. (c) Rurack, K. Spectrochim. Acta 2001, 57A, 2161.
10. (d) Valeur, B.; Leray, I. Coord. Chem. Rev. 2000, 205, 3.
11. Formercury chemosensors, see: (a) Yang, H.; Zhou, Z.; Huang, K.; Yu, M.; Li, F.; Yi, T.; Huang, C. Org. Lett. 2007, 9, 4729.
12. (b) Coskun, A.; Yilmaz, M. D.; Akkaya, E. U. Org. Lett. 2007, 9, 607.
13. (c) Ko, S.-K.; Yang, Y.-K.; Tae, J.; Shin, I. J. Am. Chem. Soc. 2006, 128, 14150.
14. (d) Zheng, H.; Qian, Z.-H.; Xu, L.; Yuan, F.-F.; Lan, L.-D.; Xu, J.-G. Org. Lett. 2006, 8, 859.
15. (e) Matsushita, M.; Meijler, M. M.; Wirsching, P.; Lerner, R. A.; Janda, K. D. Org. Lett. 2005, 7, 4943.
16. For lead-specified probes, see: (f) He, Q.; Miller, E. W.; Wong, A. P.; Chang, C. J. J. Am. Chem. Soc. 2006, 128, 9316.
17. (g) Kwon, J. Y.; Jang, Y. J.; Lee, Y. J.; Kim, K. M.; Seo, M. S.; Nam, W.; Yoon, J. J. Am. Chem. Soc. 2005, 127, 10107.
18. (h) Chen, C. T.; Huang, W. P. J. Am. Chem. Soc. 2002, 124, 6246.
19. For copper-responsive fluorescent sensors, see: (i) Weng, Y.-Q.; Yue, F.; Zhong, Y.-R.; Ye, B.-H. Inorg. Chem. 2007, 46, 7749.
20. (j) Zeng, L.; Miller, E. W.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. J. Am. Chem. Soc. 2006, 128, 10.
21. (k) Royzen, M.; Dai, Z.; Canary, J. W. J. Am. Chem. Soc. 2005, 127, 1612.
22. (a) Bronson, R. T.; Michaelis, D. J.; Lamb, R. D.; Husseini, G. A.; Farnsworth, P. B.; Linford, M. R.; Izatt, R. M.; Bradshaw, J. S.; Savage, P. B. Org. Lett. 2005, 7, 1105.
23. (b) Gunnlaugsson, T.; Lee, T. C.; Parkesh, R. Tetrahedron 2004, 60, 11239.
24. (c) Gunnlaugsson, T.; Lee, T. C.; Parke, R. Org. Lett. 2003, 5, 4065.
25. (d) Costero, A. M.; Andreu, R.; Monrabal, E.; Martinez-Manez, R.; Sancenon, F.; Soto, J. J. Chem. Soc., Dalton Trans. 2002, 1769.
26. (e) Choi, M.; Kim, M.; Lee, K. D.; Han, K. N.; Yoon, I. A.; Chung, H. J.; Yoon, J. Org. Lett. 2001, 3, 3455.
27. (a) Yunus, S.; Charles, S.; Dubois, F.; Vander Donckt, E. J. Fluoresc. 2008, 18, 499.
28. (b) Lee, H. N.; Kim, H. N.; Swamy, K. M, K.; Park, M. S.; Kim, J.; Lee, H.; Lee, K.-H.; Park, S.; Yoon, J. Tetrahedron Lett. 2008, 49, 1261.
29. (c) Liu, W.; Xu, L.; Sheng, R.; Wang, P.; Li, H.; Wu, S. Org. Lett. 2007, 9, 3829.
30. (d) Peng, X.; Du, J.; Fan, J.; Wang, J.; Wu, Y.; Zhao, J.; Sun, S.; Xu, T. J. Am. Chem. Soc. 2007, 129, 1500.
31. (e) Lu, C.; Xu, Z.; Cui, J.; Zhang, R.; Qian, X. J. Org. Chem. 2007, 72, 3554.
32. (f) Aragoni, M. C.; Area, M.; Bencini, A.; Blake, A. J.; Caltagirone, C.; Danesi, A.; Devillanova, F. A.; Garau, A.; Gelbrich, T.; Isaia, F.; Lippolis, V.; Hursthouse, M. B.; Valtancoli, B.; Wilson, C. Inorg. Chem. 2007, 46, 8088.
33. (g) Luo, H.-Y.; Jiang, J.-H.; Zhang, X.-B.; Li, C-Y.; Shen, G.-L.; Yu, R.-Q. Talanta 2007, 72, 575.
34. Chaney, R. L.; Ryan, J. A.; Li, Y.-M.; Brown, S. L. In Cadmium in Soils and Plants; McLaughlin, M. J., Singh, B. R., Eds.; Kluwer: Boston, 1999; pp 219-256.
35. (a) Dobson, S. Cadmium; Environmental Aspects; World Health Organization: Geneva, 1992.
36. (b) Friberg, L.; Elinger, C. G.; Kjellström, T. Cadmium;World Health Organization: Geneva, 1992.
37. (a) Cotton, F. A.; Wilkinson, G. Advances in Inorganic Chemistry, 5th ed.; Wiley: New York, 1988; pp 957-1358.
38. (b) Dakternieks, D. Coord. Chem. Rev. 1990, 98, 279-294.
39. (a) Mao, J.; Wang, L.; Dou, W.; Tang, X.; Yan, Y.; Liu, W. Org. Lett. 2007, 9, 4567.
40. (b) Dang, F.; Liu, W.; Zheng, J. J. Fluoresc. 2007, 17, 89.
41. Chattopadhyay, N.; Mallick, A.; Sengupta, S. J. Photochem. Photobiol. A 2006, 177, 55.
42. (a) Song, K. C.; Kim, J. S.; Park, S. M.; Chung, K.-C.; Ahn, S.; Chang, S.-K. Org. Lett. 2006, 8, 3413.
43. (b) Zhang, H.; Man, L.; Zachariasse, K. A.; Jiang, Y. Org. Lett. 2005, 7, 4217.
44. Zhang, R.; Jordan, R.; Nuyken, O. Macromol Rapid Commun. 2003, 24, 246.
45. (a) Pan, B.; Gao, F.; He, R.; Cui, D.; Zhang, Y. J. Colloid Interface Sci. 2006, 297, 151.
46. (b) Baruah, M.; Qin, W.; Vallëe, R. A. L.; Beljonne, D.; Rohand, T.; Dehaen, W.; Boens, N. Org. Lett. 2005, 7, 4377.
47. (c) Cielen, E.; Stobiecka, A.; Tahri, A.; Hoornaert, G. J.; Schryver, F. C. D.; Gallay, J.; Vincent, M. J. Chem. Soc., Perkin Trans. 2 2002, 1197.