Click synthesis of triazole-linked calix[4]arene ionophores. Potentiometric and ESI-MS screening of ion-selectivity |
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Authors: | János B Czirok Gyula Jágerszki Klára Tóth Ágnes Révész László Drahos István Bitter |
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Institution: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, P.O. Box 91, Budapest, 1521, Hungary 2. Institute of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, P.O. Box 91, Budapest, 1521, Hungary 3. Institute of Organic Chemistry, Research Centre for Natural Sciences, Hungarian Academy of Sciences, P.O. Box 17, Budapest, 1525, Hungary
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Abstract: | A series of 1,2,3-triazole-linked calix4]arene ionophores comprised of different O-donor groups (OH, COOEt, CONEt2) attached either to the lower rim of calix or to the triazole moieties were synthesized to explore their ion-selectivity for the first time in potentiometric transduction. Plasticized PVC membrane electrodes (ISEs) were fabricated, and their potentiometric selectivities were measured toward a series of mono- and divalent metal ions. Structure-ion-selectivity relationship and the structural requirements of the coordination sphere for selective binding were established. ISEs made of calix4]arene-bis-triazoles were found generally to exhibit distinct Ag+ selectivity in the order 3 ≈ 4 > 2 > 1, indicating the beneficial effect of the carboxamide or ester groups in the complexing site. In contrast, calix4]arene-tetratriazole 5 comprised only sp 2 N-donor atoms displayed excellent Cu2+ selectivity over a series of alkali-, alkaline earth- and transition metal ions. A unique feature of the outstanding Ag+ selective electrodes made of 3 and 4 was recognized and suggested their potential application as Na+ ISEs in systems not containing silver ions. Further, the potential use of competitive ESI-MS experiments for screening the binding affinities of ionophores 3–6 to different metal ions was also demonstrated. |
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