Substituent control of potassium and rubidium uptake by asymmetric calix[4]-thiacalix[4]tubes |
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Authors: | Khomich Elena Kashapov Marat Vatsouro Ivan Shokova Elvira Kovalev Vladimir |
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Institution: | Laboratory of Macrocyclic Receptors, Chemistry Department, Moscow State University, Lenin's Hills, 119992, Moscow, Russia. |
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Abstract: | Herein we report on the synthesis and ionophore properties of the first asymmetric p-tert-butylcalix4]-p-R-thiacalix4]tubes 7a-c (R = t-Bu, H, 1-adamantyl). The target compounds were obtained by the condensation of tosyloxyethoxy-p-tert-butylcalix4]arene with the corresponding p-R-thiacalix4]arenes in the presence of K2CO3 in acetonitrile. The complexation with sodium, potassium and rubidium iodides was studied in CDCl3-CD3OD (4:1) medium by means of 1H NMR measurements. It was found that the ionophore properties of calixtubes 7a-c are controlled by the character of the substituents at the upper rim of the thiacalix4]arene fragment and it was shown that only the molecular tube 7c with an adamantane-containing thiacalixarene unit is capable of quantitatively binding potassium (swiftly) and rubidium (slowly) cations. |
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