Temperature-Dependent and pH-Responsive Pillar[5]arene-Based Complexes and Hydrogen-Bond-Based Supramolecular Pentagonal Boxes in Water.,Chemistry - A European Journal

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Temperature-Dependent and pH-Responsive Pillar[5]arene-Based Complexes and Hydrogen-Bond-Based Supramolecular Pentagonal Boxes in Water.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-04-07 , DOI: 10.1002/chem.202000972
Maya Hadar ₁ , Dana Kaizerman-Kane ₁ , Yossi Zafrani ₂ , Yoram Cohen ₁

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Supramolecular systems in water are of paramount importance and those based on hydrogen bonds are both intriguing and scarce. Here, after studying the peculiar host–guest complexes formed between per‐dimethylamino‐pillar[5]arene (1) and the bis‐sulfonates 2 a–c, we describe the formation of the first hydrogen‐bond‐based supramolecular pentagonal boxes (SPBs), which are stable in water. These pH‐responsive SPBs are constructed from 1 as a body, benzene polycarboxylic acids 3 a,b as lid compounds, and 2 a–c as guests. We demonstrate that encapsulation of 2 a–c in pillar[5]arene 1 and in the highly stable water‐soluble SPBs, that is, 1(3 a)₂ and 1(3 b)₂, is both temperature and pH dependent and, quite interestingly, depends, on the nature of the lid compounds used for capping the boxes even at high pH. We also highlight the difference in the ¹H NMR characteristics of 2 b and 2 c in the cavity of 1 and the SPBs.

中文翻译：

温度依赖性和pH响应的[5]芳烃基络合物和氢键基超分子五角形盒。

水中的超分子系统至关重要，而基于氢键的系统则既有趣又稀缺。在这里，我们研究了过二甲氨基氨基[5]芳烃（1）和双磺酸盐2 a – c之间形成的奇特的主体-客体复合物，我们描述了第一个基于氢键的超分子五角形盒的形成（ SPBs），在水中稳定。这些pH响应性SPB由1作为主体，由苯多元羧酸3a，b作为盖化合物和2a – c作为客体构成。我们证明了在支柱[5]芳烃中封装2 a – c1和在高度稳定的水溶性SPB中，即1（3 a）₂和1（3 b）₂，都取决于温度和pH值，并且非常有趣的是，取决于所用盖化合物的性质即使在高pH值下也要盖好盒子。我们还强调了1和SPB腔中2 b和2 c的¹ H NMR特性差异。

更新日期：2020-04-07

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