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Binding properties of calix[4]arene-amides and thioamides and their application in ion
selective electrodes
a
V. Hubscher-Bruder a , J. Kulesza a,b , F. Arnaud-Neu a b
, M. Bocheńska
Department of Analytical Sciences”, IPHC, UMR 7178 (CNRS-UDS), ECPM,
25 rue Becquerel, 67087 Strasbourg Cedex 02, France
b
Department of Chemical Technology, Technical University of Gdansk
ul. Narutowicza 11/12, 80-264 Gdansk, Poland
At present, the importance of detecting and controlling the toxic heavy metals (such as
Cd 2+ or Pb 2+
) in waters, is extremely important, being a challenge for chemists who design
and synthesize selective ligands for these cations.
We report here the study of calix[4]arene-thioamides as potential sensing material for
transition and heavy metal cations. By introducing soft sulphur atoms into the structure of the
calix[4]arene, the preference for binding heavy and transition metal cations, toxic for human
beings, was expected. Although some examples of calixarene-thioamides applications are
known from the literature, only few publications deal with, for instance, stability constants
1-3
determination which is important in studying new ligands properties.
The interactions of these ligands with several representative cations (Na + , Ca 2+ , Gd 3+ ,
Ag + , Cd 2+ , Pb 2+ , Zn 2+ and Cu 2+ ) were studied using different techniques: liquid-liquid
extraction, 1
H NMR, X-ray diffractometry, UV spectrophotometry, potentiometry and
microcalorimetry. The properties of calix[4]arene-thioamides were compared with their
corresponding calix[4]arene-amides. Some of these thioamides derivatives were used as
active materials in ion-selective membrane electrodes (ISEs).
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M. J. Schwing-Weill, J. Chem. Soc., Perkin Trans. 2, 1997, 575
[2] M. G. Drew, P. D. Beer, M. I. Ogden, Acta Cryst., 1997, C53, 472
[3] K. No, J. H. Lee, S. H. Yang, S. H. Yu, M. H. Cho, M. J. Kim, J. S. Kim, J. Org., 2002, 67, 3165