A new fluorescent fluoride chemosensor based on conformational restriction of a biaryl fluorophore

Tetrahedron Letters

Volumn 43, Issue 52, 2002, Pages 9637-9640

  Lee, Dong Hoon ^a   Im, Ja Hyun ^a   Lee, Jae Han ^a   Hong, Jong In ^a,b  

^a Seoul National University   (South Korea)

^b Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORIDE; HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIOUREA DERIVATIVE;

ARTICLE; COMPLEX FORMATION; CONFORMATION; FLUORESCENCE; HYDROGEN BOND; SENSOR;

EID: 0037164686     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02443-7     Document Type: Article

References (38)

1. Beer P.D., Gale P.A. Angew. Chem., Int. Ed. 40:2001;486.
2. Fabbrizzi L., Licchelli M., Labaioli G. Coord. Chem. Rev. 205:2000;85.
3. Beer P.D., Cadman J. Coord. Chem. Rev. 205:2000;135.
4. Schmidtchen F.P., Berger M. Chem. Rev. 97:1997;1609; Comprehensive Supra-molecular Chemistry; Lehn, J.-M. Chair ed.; Atwood, J. L.; Davies, J. E. D.; MacNicol, D. D.; Vögtle, F., Eds.; Pergamon: Oxford, 1996; Vol. 1 Chemosensors of Ion and Molecular Recognition; Desvergne, J.-P.; Czarnik, A. W., Eds.; Kluwer: Dordrecht, 1997; Vol. 492.
5. Niikura K., Anslyn E.V. J. Am. Chem. Soc. 120:1998;8533.
6. Metzger A., Anslyn E.V. Angew. Chem., Int. Ed. 37:1998;649.
7. Gale P.A., Twyman L.J., Handlin C.I., Sessler J.L. Chem. Commun. 1999;1851.
8. Anzenbacher P. Jr., Jursíková K., Sessler J.L. J. Am. Chem. Soc. 122:2000;9350.
9. Mizukami S., Nagano T., Urano Y., Odani A., Kikuchi K. J. Am. Chem. Soc. 124:2002;3920-3925.
10. Valence D.H., Czarnik A.W. J. Am. Chem. Soc. 116:1994;9397.
11. Gunnlaugsson T., Davis A.P., Glynn M. Chem. Commun. 2001;2556.
12. Kim S.K., Yoon J. Chem. Commun. 2001;770.
13. Nishizawa S., Teramae N. J. Chem. Soc., Perkin Trans. 2. 2002;866.
14. Nishizawa S., Teramae N. J. Chem. Soc., Perkin Trans. 2. 1998;2325.
15. Choi K., Hamilton A.D. Angew. Chem., Int. Ed. 40:2001;3912.
16. Nishizawa S., Kaneda H., Uchida T., Teramae N. J. Chem. Soc., Perkin Trans. 2. 11:1998;2325.
17. Nishizawa S., Kaneda H., Kato Y., Teramae N. J. Am. Chem. Soc. 121:1998;9463.
18. De Santis G., Fabrizzi L., Licchelli M., Poggi A., Taglietti A. Angew. Chem., Int. Ed. 35:1996;202.
19. Mcfarland S.A., Finney N.S. J. Am. Chem. Soc. 124:2002;1178.
20. Mcfarland S.A., Finney N.S. J. Am. Chem. Soc. 123:2001;1260.
21. Mello J.V., Finney N.S. Angew. Chem., Int. Ed. 40:2001;1536.
22. Watanabe S., Onogawa O., Komatsu Y., Yoshida K. J. Am. Chem. Soc. 120:1998;229.
23. Sandanayake K., Nakashima K., Shinkai S. Chem. Commun. 1994;1621.
24. Ta-keuchi M., Mizuno T., Shinmori H., Shinkai S. Tetrahedron. 52:1996;1195.
25. Takeuchi M., Yoda S., Imada T., Shinkai S. Tetrahedron. 53:1997;8335.
26. Yamaguchi S., Akiyama S., Tamao K. J. Am. Chem. Soc. 123:2001;11372.
27. Jimenez D., Soto J. Tetrahedron Lett. 43:2002;2823.
28. Dreisbuch R.H. Handbook of Poisoning. 1980;Lange Medical Publishers, Los Altos, CA.
29. Hiatt R.R., Shaio M.-J., Georges F. J. Org. Chem. Soc. 44:1979;3265.
30. Taub B., Hino J.B. J. Org. Chem. Soc. 26:1961;5238.
31. Nishizawa S., Bühlmann P., Umezawa Y. Tetrahedron Lett. 36:1995;6483.
32. 2=442.2225.
33. - resulted in broad emission enhancement around 450 nm.
34. Kavallieratos K., Bertao C.M., Crabtree R.H. J. Org. Chem. 64:1999;1675.
35. Conners K.A. Binding Constants. 1987;John Wiley and Sons, New York.
36. 3, THF, MeCN. We thank a referee for advice.
37. Lakowicz J.R. Principles of Fluorescence Spectroscopy. 1:1996;701 Plenum Press, New York.
38. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., Still W.C. J. Comput. Chem. 11:1990;440.