Novel biscrowns 1 and 2 were synthesized from 13-membered azobenzocrown ethers containing bromoalkylenoxy chains in para position relative to the azo group. The synthesized diester molecules are dodecylmethylmalonic acid derivatives differing by the linker length. The synthesized compounds have the potential of being used as sodium ionophores in ion-selective electrodes. They were characterized and used as ionophores in classic and miniature, solid contact (screen-printed and glassy carbon) membrane ion-selective electrodes. Compound 3, a similar monoester derivative of 13-membered azobenzocrown, was synthesized and used in membrane electrodes for comparison. Lipophilicity of new ionophores was determined by TLC. Lipophilicity of bis(azobenzocrown)s was found to be within the range of logPTLC = 12–13. It was observed that the particularly important selectivity coefficients logKNa,K determined for new electrodes, being logKNa,K = −2.5 and −2.6 (SSM, 0.1 M), are better than those of the electrodes featuring seven out of the nine commercially available sodium ionophores. It was concluded that the ionophore 1 creates, in acetone, with sodium iodide, complex of 1:1 stoichiometry (sandwich complex) with stability constant (logK) ca. 3.0.

中文翻译：

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具有十二烷基甲基丙二酰连接基的新型双（偶氮苯冠）作为钠选择性电位传感器的离子载体


新型双冠1和2是由13元偶氮苯并冠醚合成的，其中溴亚烷氧基链位于偶氮基团的对位。合成的二酯分子是十二烷基甲基丙二酸衍生物，其接头长度不同。合成的化合物具有用作离子选择性电极中的钠离子载体的潜力。它们被表征并用作经典和微型固体接触（丝网印刷和玻璃碳）膜离子选择性电极中的离子载体。合成了化合物3，一种类似的13元偶氮苯冠单酯衍生物，并将其用于膜电极中进行比较。新离子载体的亲脂性通过TLC测定。发现双(偶氮苯冠)的亲脂性在 logPTLC = 12–13 的范围内。据观察，为新电极确定的特别重要的选择性系数 logKNa,K，即 logKNa,K = -2.5 和 -2.6 (SSM，0.1 M)，优于具有 9 种市售钠中的 7 种电极的选择性系数离子载体。结论是，离子载体 1 在丙酮中与碘化钠形成 1:1 化学计量的复合物（夹心复合物），稳定常数 (logK) 约为 1。 3.0。