Novel chiral fluorescent chemosensors for malate and acidic amino acids based on two-arm thiourea and amide

Canadian Journal of Chemistry

Volumn 86, Issue 2, 2008, Pages 170-176

  Huang, Xiao Huan ^a   He, Yong Bing ^a   Chen, Zhi Hong ^a   Hu, Chen Guang ^a   Qing, Guang Yan ^a  

^a WUHAN UNIVERSITY   (China)

Author keywords

Chiral chemosensor; Enantioselective recognition; Fluorescence; Malate

Indexed keywords

AMIDES; AMINO ACIDS; ANTHRACENE; CHIRALITY; FLUORESCENCE;

CHIRAL CHEMOSENSORS; ENANTIOSELECTIVE RECOGNITION; MALATE;

CHEMICAL SENSORS;

EID: 39449137750     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V07-147     Document Type: Article

References (34)

1. (a) Y. Kubo, S. Maeda, S. Tokita, and M. Kubo. Nature, 382, 522 (1996);
2. (b) C.P. McCoy, J.T. Rademacher, and T.E. Rice. Chem. Rev. 97, 1515 (1997);
3. (c) P.D. Beer and P.A. Gale. Angew. Chem. Int. Ed. 40, 486 (2001);
4. (d) M.R. Martinez and F. Sancenon. Chem. Rev. 103, 4419 (2003);
5. (e) L. Pu. Chem. Rev. 104, 1687 (2004).
6. (a) A.P. Davis and R.S. Wareham. Angew. Chem. Int. Ed. 38, 2978 (1999);
7. (b) S.Y. Liu, L. Fang, Y.B. He, W.H. Chan, K.T. Yeung, Y.K. Cheng, and R.H. Yang. Org. Lett. 7, 5825 (2005);
8. (c) Y.S. Zheng and C. Zhang. Org. Lett. 6, 1189 (2004);
9. (d) T.J. Liu, Y.J. Chen, K.S. Zhang, D. Wang, D.W. Guo, and X.Z. Yang. Chirality, 13, 595 (2001);
10. (e) R. Corradini, A. Dossena, R. Marchelli, A. Panagia, G. Sartor, M. Saviano, A. Lombardi, and V. Pavone. Chem. Eur. J. 2, 373 (1996).
11. (a) A. Ojida, Y. Mito-oka, M. Inoue, and I. Hamachi. J. Am. Chem. Soc. 124, 6256 (2002);
12. (b) J.Y Kwon, Y.J. Jang, S.K. Kim, K.H. Lee, J.S. Kim, and J. Yoon. J. Org. Chem. 69, 5155 (2004).
13. (a) M.S. Goodman, A.D. Hamilton, and J. Weiss. J. Am. Chem. Soc. 117, 8447 (1995);
14. (b) B.R. Linton, M.S. Goodman, E. Fan, S.A. van Arman, and A.D. Hamilton. J. Org. Chem. 66, 7313 (2001);
15. (c) K. Kacprzak and J. Gawronski. Chem. Commun. (Cambridge), 1532 (2003);
16. (d) J.L. Wu, Y.B. He, Z.Y. Zeng, L.H. Wei, L.Z. Meng, and T.X. Yang. Tetrahedron, 60, 4309 (2004).
17. (a) D.H. Lee, K.H. Lee, and J.I. Hong. Org. Lett. 3, 5 (2001);
18. (b) P. Piatek and J. Jurczak. Chem. Commun. (Cambridge), 2450 (2002).
19. (a) T. Gunnlaugsson, A.P. Davis, E.J. O'Brient, and M. Glynn. Org. Lett. 4, 2449 (2002);
20. (b) T. Gunnlaugsson, A.P. Davis, J.E. O'Brien, and M. Glynn. Org. Biomol. Chem. 3, 48 (2005).
21. (a) G.Y. Qing, Y.B. He, Z.H. Chen, X.J. Wu, and L.Z. Meng. Tetrahedron: Asymmetry, 17, 3144 (2006);
22. (b) A. Gonzalez-Alvarez, I. Alfonso, P. Diaz, E. Garcia-Espana, and V Gotor. Chem. Commun. (Cambridge, U.K.), 1227 (2006).
23. (a) J. Bourson, J. Pouget, and B. Valeur. J. Phys. Chem. 97, 4552 (1993);
24. (b) D.H. Lee, H.Y. Lee, K.H. Lee, and J.I. Hong. Chem. Commum. (Cambridge), 1188 (2001).
25. S. Nishizawa, R. Kato, T. Hayashita, and N. Teramae. Anal. Sci. 14, 595 (1998).
26. (a) D. Braun, W. Retting, S. Delmond, J.F. Letard, and R. Lapouyade. J. Phys. Chem. A, 101, 6836 (1997);
27. (b) J.P. Malval and R. Lapouyade. Helv. Chim. Acta. 84, 2439 (2001);
28. (c) F.Y. Wu and Y.B. Jiang. Chem. Phys. Lett. 355, 438 (2002).
29. (a) A.P. deSilva, H.Q.N. Gunaratne, T. Gunnlaugsson., A.J.M. Huxley, C.P. McCoy, J.T. Rademacher, and T.E. Rice. Chem. Rev. 97, 1515 (1997);
30. (b) R. Martinez and F. Sancen. Chem. Rev. 103, 4419 (2003).
31. H.J. Schneider and A.K. Yatsimirsky. Principles and methods in supramolecular chemistry. John Wiley & Sons, NY 2000.
32. B. Valeur, J. Pouget, and J. Bourson. J. Phys. Chem. 96, 6545 (1992).
33. (a) W.H. Pirkle and T.C. Pochapsky. Chem. Rev. 89, 347 (1989);
34. (b) T. Grady, S.J. Harris, M.R. Smyth, D. Diamond, and P. Hailey. Anal. Chem. 68, 3775 (1996).