A naphthalimide-calixarene as a two-faced and highly selective fluorescent chemosensor for Cu2+ or F-

Tetrahedron Letters

Volumn 48, Issue 52, 2007, Pages 9151-9154

  Xu, Zhaochao ^a   Kim, Suki ^a   Kim, Ha Na ^a   Han, Su Jung ^a   Lee, Chongmok ^a   Kim, Jong Seung ^b   Qian, Xuhong ^c   Yoon, Juyoung ^a  

^a Ewha Womans University   (South Korea)

^b Korea University   (South Korea)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; CALIXARENE; COPPER; FLUORINE; IMIDE; METAL ION; NAPHTHALIMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLORIMETRY; COLUMN CHROMATOGRAPHY; COMPLEX FORMATION; FLUORESCENCE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; SYNTHESIS; TITRIMETRY;

EID: 36448980981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.109     Document Type: Article

References (56)

1. Kim S.K., Kim H.N., Zhu X., Lee H.N., Lee H.N., Soh J.H., Swamy K.M.K., and Yoon J. Supramol. Chem. 19 (2007) 221
2. Yoon J., Kim S.K., Singh N.J., and Kim K.S. Chem. Soc. Rev. 35 (2006) 355
3. Gunnlaugsson T., Glynn M., Tocci G.M., Kruger P.E., and Pfeffer F.M. Coord. Chem. Rev. 250 (2006) 3094
4. Martínez-Máñez R., and Sancanón F. Chem. Rev. 103 (2003) 4419
5. Beer P.D., and Gale P.A. Angew. Chem., Int. Ed. 40 (2001) 486
6. Kim J.S., and Quang D.T. Chem. Rev. 107 (2007) 3780
7. Callan J.F., de Silva A.P., and Magri D.C. Tetrahedron 61 (2005) 8551
8. de Silva A.P., Gunaratne H.Q.N., Gunnlaugsson T.A., Huxley T.M., McCoy C.P., Rademacher J.T., and Rice T.E. Chem. Rev. 97 (1997) 1515
9. Czarnik A.W. Acc. Chem. Res. 27 (1994) 302
10. Kirk K.L. Biochemistry of the Halogens and Inorganic Halides (1991), Plenum Press, New York p 58
11. Kleerekoper M. Endocrinol. Metab. Clin. North Am. 27 (1998) 441
12. Zhao Y.-P., Zhao C.-C., Wu L.-Z., Zhang L.-P., Tung C.-H., and Pan Y.-J. J. Org. Chem. 71 (2006) 2143
13. Jun E.J., Swamy K.M.K., Bang H., Kim S.-J., and Yoon J. Tetrahedron Lett. 47 (2006) 3103
14. Kim S.K., Bok J.H., Bartsch R.A., Lee J.Y., and Kim J.S. Org. Lett. 7 (2005) 4839
15. Kwon J.Y., Jang Y.J., Kim S.K., Lee K.-H., Kim J.S., and Yoon J. J. Org. Chem. 69 (2004) 5155
16. Kim S.Y., and Hong J.-I. Org. Lett. 9 (2007) 3109
17. Swamy K.M.K., Lee Y.J., Lee H.N., Chun J., Kim Y., Kim S.-J., and Yoon J. J. Org. Chem. 71 (2006) 8626
18. Kubo Y., Kobayashi A., Ishida T., Misawa Y., and James T.D. Chem. Commun. (2005) 2846
19. Peng X., Wu Y., Fan J., Tian M., and Han K. J. Org. Chem. 70 (2005) 10524
20. Liu Z.-Q., Shi M., Li F.-Y., Fang Q., Chen Z.-H., Yi T., and Huang C.-H. Org. Lett. 7 (2005) 5481
21. Thiagarajan V., Ramamurthy P., Thirumalai D., and Ramakrishnan V.Y. Org. Lett. 7 (2005) 657
22. Esteban-Gómez D., Fabbrizzi L., and Liccheli M. J. Org. Chem. 70 (2005) 5717
23. Liu B., and Tian H. J. Mater. Chem. (2005) 2681
24. Curiel D., Cowley A., and Beer P.D. Chem. Commun. (2005) 236
25. Xu G., and Tarr M.A. Chem. Commun. (2004) 1050
26. Cho E.J., Moon J.W., Ko S.W., Lee J.Y., Kim S.K., Yoon J., and Nam K.C. J. Am. Chem. Soc. 125 (2003) 12376
27. for other references, see 1d.
28. Li Y., Cao L., and Tian H. J. Org. Chem. 71 (2006) 8279
29. Gunnlaugsson T., Kruger P.E., Lee T.C., Parkesh R., Pfeffer F.M., and Hussey G.M. Tetraehdron Lett. 44 (2003) 6575
30. Gunnlaugsson T., Kruger P.E., Jensen P., Pfeffer F.M., and Hussey G.M. Tetraehdron Lett. 44 (2003) 6575
31. Xiang Y., Tong A., Jin P., and Ju Y. Org. Lett. 8 (2006) 2863
32. Lee Y.J., Seo D., Kwon J.Y., Son G., Park M.S., Choi Y.-H., Soh J.H., Lee H.N., Lee K.D., and Yoon J. Tetrahedron 62 (2006) 12340
33. Martínez R., Zapata F., Espinosa A., Tárraga A., and Molina P. J. Org. Chem. 8 (2006) 3252
34. Kim S.H., Kim J.S., Park S.M., and Chang S.-K. Org. Lett. 8 (2006) 371
35. Zeng L., Miller E., Pralle A., Isacoff E.Y., and Chang C.J. J. Am. Chem. Soc. 128 (2006) 10
36. Qi X., Jun E.J., Xu L., Kim S.-J., Hong J.S.J., Yoon Y.J., and Yoon J. J. Org. Chem. 71 (2006) 2881
37. Weng Z.-C., Yang R., He H., and Jiang Y.-B. Chem. Commun. (2006) 106
38. Jun E.J., Won H.N., Kim J.S., Lee K.-H., and Yoon J. Tetrahedron Lett. 47 (2006) 4577
39. Jang Y.J., Moon B.-S., Park M.S., Kang B.-G., Kwon J.Y., Hong J.S.J., Yoon Y.J., Lee K.D., and Yoon J. Tetrahedron Lett. 47 (2006) 2707
40. Kubo Y., Ishida T., Kobayashi A., and James T.D. J. Mater. Chem. 15 (2005) 2889
41. Royzen M., Dai Z., and Canary J.W. J. Am. Chem. Soc. 127 (2005) 1612
42. for other references, see 2b.
43. Lu C., Xu Z., Cui J., Zhang R., and Qian X. J. Org. Chem. 72 (2007) 3554
44. Xu Z., Qian X., Cui J., and Zhang R. Tetrahedron 62 (2006) 10117
45. Xu Z., Qian X., and Cui J. Org. Lett. 7 (2005) 3029
46. Xu Z., Xiao Y., Qian X., Cui J., and Cui D. Org. Lett. 7 (2005) 889
47. In: Asfari Z., Böhmer V., Harrowfield J., and Vicens J. (Eds). Calixarenes 2001 (2001), Kluwer Academic, Dordrecht, The Netherlands
48. Gutsche C.D. In: Stoddart J.F. (Ed). Calixarene: Monographs in Supramolecular Chemistry Vol. 1 (1989), Royal Society of Chemistry, Cambridge, UK
49. Liu Y., Wang H., Wang L., Li Z., Zhang H., and Zhang Q. Tetrahedron 59 (2003) 7967
50. + 984.5891, found 984.5897.
51. Conners K.A. Binding Constants (1987), Wiley, New York
52. Association constants were obtained using the computer program ENZFITTER, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, United Kingdom.
53. Esteban-Gómez D., Fabbrizzi L., and Licchelli M. J. Org. Chem. 70 (2005) 5717
54. Cho E.J., Ryu B.J., Lee Y.J., and Nam K.C. Org. Lett. 7 (2005) 2607
55. Boiocchi M., Del Boca L., Esteban-Gómez D., Fabbrizzi L., Licchelli M., and Monzani E. J. Am. Chem. Soc. 126 (2004) 16507
56. Jose D.A., Kumar D.K., Ganguly B., and Das A. Org. Lett. 6 (2004) 3445