Selective metal detection in an unsymmetrical 1,3-alternate calix[4]biscrown chemosensor

Tetrahedron Letters

Volumn 47, Issue 8, 2006, Pages 1237-1240

  Bok, Ju Han ^a   Kim, Hyun Jung ^a   Lee, Jeong Won ^a   Kim, Sung Kuk ^a   Choi, Jung Kyu ^a   Vicens, Jacques ^b   Kim, Jong Seung ^a  

^a Dankook University   (South Korea)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 NAPHTHALENE; CALIX[4]CROWN; CALIXARENE; LEAD; NAPHTHALENE DERIVATIVE; OXYGEN; POTASSIUM ION; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; FLUORESCENCE; POSITRON EMISSION TOMOGRAPHY; SENSOR; SYNTHESIS;

EID: 31044435194     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.096     Document Type: Article

References (31)

1. J.F. Callan, A.P. de Silva, and D.C. Magri Tetrahedron 61 2005 8551
2. J.P. Desvergne A.W. Czarnik Chemosensors of Ion and Molecular Recognition NATO ASI Series 1997 Kluwer Academic Dordrecht
3. Luminescent sensors, Fabbrizzi, L., Ed.; Special Issue Coord. Chem. Rev. 2000, 205, pp 1-232.
4. B. Valeur Molecular Fluorescence. Principles and Applications 2002 Wiley-VCH Weinheim
5. J.R. Lakowicz Principles of Fluorescence Spectroscopy 2nd ed. 1999 Plenum New York
6. Z. Asfari V. Böhmer J. Harrowfield J. Vicens Calixarenes 2001 2001 Kluwer Academic Dordrecht, Netherlands
7. C.D. Gutsche J.F. Stoddart Calixarenes Revisited. Monographs in Supramolecular Chemistry 1998 Royal Society of Chemistry London
8. J. Vicens V. Böhmer Calixarenes: A Versatile Class of Macrocyclic Compounds 1991 Kluwer Academic Dordercht, Netherlands
9. C.D. Gutsche J.F. Stoddart Calixarenes, Monographs in Supramolecular Chemistry No. 3 1989 Royal Society of Chemistry London
10. A. Casnati, R. Ungaro, Z. Asfari, and J. Vicens Z. Asfari V. Böhmer J. Harrowfield J. Vicens Calixarenes 2001 2001 Kluwer Academic Dordrecht, Netherlands Chapter 20
11. B. Pulpoka, and J. Vicens J. Nano. Bio. Tech. 1 2005 55
12. For some studies on fluorescent 1,3-calix[4]biscrowns, see: H.-F. Ji, G.M. Brown, and R. Dabestani Chem. Commun. 1999 609
13. H.-F. Ji, R. Dabestani, G.M. Brown, and R.L. Hettich J. Chem. Soc., Perkin Trans. 2 2002 585
14. I. Leray, Z. Asfari, J. Vicens, and B. Valeur J. Chem. Soc., Perkin Trans. 2 2002 1429
15. I. Leray, Z. Asfari, J. Vicens, and B. Valeur J. Fluor. 2004 451
16. J.-P. Malval, I. Leray, and B. Valeur New J. Chem. 29 2005 1089
17. S.H. Lee, J.Y. Kim, J. Ko, J.Y. Lee, and J.S. Kim J. Org. Chem. 69 2002 2348
18. J.S. Kim, O.J. Shon, J.A. Rim, S.K. Kim, and J. Yoon J. Org. Chem. 67 2002 2905
19. J.S. Kim, K.H. Noh, S.H. Lee, S.K. Kim, S.K. Kim, and J. Yoon J. Org. Chem. 68 2003 597
20. S.H. Lee, J.Y. Kim, J. Ko, S.H. Lee, and J.S. Kim J. Org. Chem. 69 2004 2902
21. S.H. Lee, J.Y. Kim, S.K. Kim, J.H. Lee, and J.S. Kim Tetrahedron 60 2004 5171
22. S.K. Kim, S.H. Lee, J.Y. Lee, J.Y. Lee, R.A. Bartsch, and J.S. Kim J. Am. Chem. Soc. 126 2004 16499
23. 3CN. After calculating the concentrations of the free ligands and complexed forms of 1-3 from the fluorescence titration experiments, the association constants were obtained using the computer program enzfitter.
24. C. Hill, J.F. Dozol, V. Lamare, H. Rouquette, S. Eymard, B. Tournois, J. Vicens, Z. Asfari, and C. Bressot J. Incl. Phenom. 19 1994 399 408
25. Z. Asfari, C. Bressot, J. Vicens, C. Hill, J.F. Dozol, H. Rouquette, S. Eymard, V. Lamare, and B. Tournois Anal. Chem. 67 1995 3133
26. E. Ghidini, F. Ugozzoli, R. Ungaro, S. Harkema, A.A. El-Fadl, and D.N. Reinhoudt J. Am. Chem. Soc. 112 1990 6979
27. A. Arduini, M. Fabbi, M. Mantovani, L. Mirone, A. Pochini, A. Secchi, and R. Ungaro J. Org. Chem. 60 1995 1454
28. Ditosylate 4 was prepared from commercial 1,5-dihydroxynaphthalene as described for the related ditosylate from 2,3-dihydroxynaphthalene, see: Z. Asfari, V. Lamare, J.F. Dozol, and J. Vicens Tetrahedron Lett. 40 1999 691
29. The complexation of two cations by calix[4]biscrowns has been observed several times (see Ref. 5c and references in) and it was shown that the complete formation of binuclear species needs more than 2 equiv of metal, see, for example: F. Arnaud, Z. Asfari, B. Souley, and J. Vicens New J. Chem. 20 1996 453
30. Association constants were obtained using the computer program enzfitter, available from Elsevier-BIOSOFT, 68 Hills Road, Cambridge CB2 1LA, United Kingdom.
31. K.A. Connors Binding Constants 1987 Wiley New York