Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode

Koji Suzuki, Dwi Siswanta, Takeshi Otsuka, Tsuyoshi Amano, Takafumi Ikeda, Hideaki Hisamoto, Ryoko Yoshihara, Shigeru Ohba

研究成果: Article査読

43 被引用数 (Scopus)

抄録

A novel ammonium ionophore, which exhibits superior NH4+ selectivity compared with that of the natural antibiotic nonactin, was successfully designed and synthesized based on a 19-membered crown compound (TD19C6) having three decalino subunits in the macrocyclic system. This bulky decalino subunit is effective for (1) increasing the structural rigidity of the cyclic compound, (2) introducing the 'block-wall effect', which prevents forming a complex with a large ion, and (3) increasing the lipophilicity of the ionophore molecule. In the ammonium ionophore design, the first factor contributes to increasing the NH4+ selectivity relative to smaller ions such as Li+, Na+, or even the closest size, K+, and the second factor increases the NH4+ selectivity over larger ions such as Rb+ and Cs+. The X-ray structural analysis proved that TD19C6 forms a size-fit complex with NH4+ in its crown ring cavity. As an application of this ionophore, an ion sensor (ion-selective electrode) was prepared, which exhibited NH4+ to K+ and Na+ selectivity of 10 and 3000 times, respectively. This electrode showed a better performance compared to the electrode based on nonactin, which is the only ammonium ionophore presently used in practical applications.

本文言語English
ページ(範囲)2200-2205
ページ数6
ジャーナルAnalytical Chemistry
72
10
DOI
出版ステータスPublished - 2000 5月 15

ASJC Scopus subject areas

  • 分析化学

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