Abstract
A new calix[4]arene-based fluorescent compound with two thio-ether groups as ionophore and one 3-alkoxy-2-naphthoic acid moiety as fluorophore has been designed, which exhibited highly selective binding of Cu 2+ over alkali, alkaline earth and some transition metal ions, including Co 2+, Ni 2+, Zn 2+, Mn 2+, Cd 2+, Pb 2+, Hg 2+, Ag +, Cu +, in CH 3OH–H 2O (2:1) within wide pH region. Moreover, the change of pH induces the consecutive quenching/revival of the fluorescence, with a concomitant distinct difference of the fluorescence quantum yield. In consequence, this system could be considered as a molecular switch.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
(a) Holm R.H., Kennepohl P., and Solomon E.I.: Chem . Rev . 96 ,(1996)2239; (b) Kaim W. and Rall J.: Angew . Chem . Int . Ed . Engl . 35 , 43 (1996)
M. Beltramello M. Gatos F. Mancin P. Tecilla U. Tonellato (2001) Tetrahedron Lett. 42 9143 Occurrence Handle10.1016/S0040-4039(01)01965-7 Occurrence Handle1:CAS:528:DC%2BD3MXptVGms7g%3D
L. Fabbrizzi M. Licchelli P. Pallavicini A. Perotti D. Sacchi (1994) Angew. Chem. Int. Ed. Engl. 33 1975 Occurrence Handle10.1002/anie.199419751
A. Torrado G.K. Walkup B. Imperiali (1998) J. Am. Chem. Soc. 120 609 Occurrence Handle10.1021/ja973357k Occurrence Handle1:CAS:528:DyaK1cXmvFWmsQ%3D%3D
R. KrämerAngew (1998) Chem. Int. Ed. Engl. 37 772 Occurrence Handle10.1002/(SICI)1521-3773(19980403)37:6<772::AID-ANIE772>3.3.CO;2-Q
R. Corradini A. Dossena G. Galaverna R. Marchelli A. Panagia G. Sartor (1997) J. Org. Chem. 62 6283 Occurrence Handle10.1021/jo970349d Occurrence Handle1:CAS:528:DyaK2sXlvFyis7o%3D
Klein G., Kaufmann D., Schurch S., and J.-L. Reymond (2001) J. Chem. Soc. Chem. Commun. 561
J. Yoon N.E. Ohler D.H. Vance W.D. Aumiller A.W. Czarnik (1997) Tetrahedron Lett. 38 3845 Occurrence Handle10.1016/S0040-4039(97)00768-5 Occurrence Handle1:CAS:528:DyaK2sXjvVKrtLk%3D
A. Singh Q. Yao L. Tong W.C. Still D. Sames (2000) Tetrahedron Lett. 41 9601 Occurrence Handle10.1016/S0040-4039(00)01714-7 Occurrence Handle1:CAS:528:DC%2BD3cXovFOmsb8%3D
B. Bodenant T. Weil M.B. Pourcel F. Fages B. Barbe I. Pianet M. Laguerre (1999) J. Org. Chem. 64 7034 Occurrence Handle10.1021/jo9904720 Occurrence Handle1:CAS:528:DyaK1MXltlansLw%3D
Y. Zheng Q. Huo P. Kele F.M. Andreopoulos S.M. Pham R.M. Lablanc (2001) Org. Lett. 3 3277 Occurrence Handle10.1021/ol0101638 Occurrence Handle1:CAS:528:DC%2BD3MXmvF2hsr8%3D Occurrence Handle11594813
Zheng Y.J., Gatt K.M.ás-Asfura, Konka V., and Leblanc R.M.(2002). Chem. Commun . 2350
G.D. Santis L. Fabbrizzi M. Licchelli C. Mangano D. Sacchi N. Sardone (1997) Inorg. Chim. Acta. 257 69 Occurrence Handle10.1016/S0020-1693(96)05452-7
Kaur S. and Kumar S. (2002). Chem. Commun 2840
(a) J.-M. Liu, Q.-Y. Zheng, J.-L. Yang, C.-F. Chen, Z.-T. Huang (2002) Tetrahedron Lett. 43 , 920; (b) Y.-D. Cao, Q.-Y. Zheng, C.-F. Chen, and Z.-T. Huang(2003) Tetrahedron Lett. 44 , 4751
C.D. Gutsche (1998) Calixarenes Revisited. Royal Society of Chemistry Cambridge
Li Z.-T. G.-Z. Ji C.-X. Zhao S.-D. Yuan H. Ding C. Huang A.-L. Du M. Wei (1999) J. Org. Chem. 64 3572 Occurrence Handle10.1021/jo9824100 Occurrence Handle11674484
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Liu, JM., Zheng, QY., Chen, CF. et al. The Design of a Highly Selective Fluorescent Chemosensor for Cu(II) within Wide pH Region and a Molecular Switch Controlled by pH. J Incl Phenom Macrocycl Chem 51, 165–171 (2005). https://doi.org/10.1007/s10847-004-6445-7
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10847-004-6445-7