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Molecular design of calixarene-based ion-selective electrodes

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Abstract

In order to obtain insights into relationships between the calix[4]arene structure and the ion selectivity in the electrode system, 20 ionophoric calix[4]arenes were synthesized and their ion selectivity (with Na+ as a standard) estimated. Among these ionophoric calix[4]arenes, 25,26,27,28-tetrakis[(ethoxycarbonyl)methoxy]-p-t-octylcalix[4]arene afforded the highest logK potNA,M value (−3.1) in the presence of 2-fluorophenyl-2′-nitrophenylether (10) as the best of 13 plasticizers. This is the first example in which the Na+/K+ selectivity exceeds a factor of 103 in the electrode system based on the neutral carrier. The high Na+ selectivity is attributed to modification of the upper rim which ostensibly has no relation with the component of the cavity. This paper demonstrates the potential relationships between the unique structure of the calix[4]arene-based ligands and selectivity performance for the design of ion-selective electrodes.

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Authors and Affiliations

  1. CHEMIRECOGNICS Project, ERATO, Research Development Corporation of Japan, Fukuoka Industrial Technology Center, Kamikoga, Chikushino, 332-1, Fukuoka 818, Japan

    Toru Sakaki, Takaaki Harada, Gang Deng, Hirosuke Kawabata, Yohko Kawahara & Seiji Shinkai

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  1. Toru Sakaki
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  2. Takaaki Harada
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  3. Gang Deng
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  4. Hirosuke Kawabata
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  5. Yohko Kawahara
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  6. Seiji Shinkai
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Sakaki, T., Harada, T., Deng, G. et al. Molecular design of calixarene-based ion-selective electrodes. J Incl Phenom Macrocycl Chem 14, 285–302 (1992). https://doi.org/10.1007/BF01045987

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  • DOI: https://doi.org/10.1007/BF01045987

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