ABSTRACT One hexaester (1) and three hexaamide derivatives (2–4) of calix[6]arenes were prepared for the first time in one synthetic step, under microwave radiation. Compounds 2 and 3 were novel ones, while ester calix[6]arene derivative 1 and amide derivative 4 were prepared previously, by conventional syntheses. Microwave-assisted syntheses shortened the reaction times from 48 to 2 h. The binding properties of calix[6]arenes towards selected lanthanide cations (La3+, Eu3+, Yb3+) were studied by spectroscopic and mass spectrometric techniques. No complexation was observed with the ester derivative, while compounds 2–4 formed 1:1 complexes. Based on spectrophotometric titrations, the stability constants of resulting complexes could only be estimated (lg K ≥ 6). Calixarene derivatives, as well as their complexes, were analysed by ESI MS and MS/MS spectrometry. Corresponding fragmentation pathways were proposed, and in some cases confirmed by MS3 experiments. The results obtained by different techniques were in accordance. Graphical abstract

中文翻译：

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杯[6]芳烃酯和酰胺衍生物的合成及其对La3+、Eu3+和Yb3+的络合亲和力

摘要 在微波辐射下，首次在一个合成步骤中制备了杯[6]芳烃的一种六酯 (1) 和三种六酰胺衍生物 (2-4)。化合物2和3是新的化合物，而酯杯[6]芳烃衍生物1和酰胺衍生物4是先前通过常规合成制备的。微波辅助合成将反应时间从 48 小时缩短到 2 小时。通过光谱和质谱技术研究了杯[6]芳烃对选定镧系元素阳离子（La3+、Eu3+、Yb3+）的结合特性。没有观察到与酯衍生物的络合，而化合物 2-4 形成了 1:1 的络合物。基于分光光度法滴定，所得配合物的稳定性常数只能估计（lg K ≥ 6）。杯芳烃衍生物，以及它们的配合物，通过 ESI MS 和 MS/MS 光谱分析。提出了相应的碎裂途径，并且在某些情况下由 MS3 实验证实。不同技术得到的结果是一致的。图形概要