Selective Capture of Thallium and Cesium by a Cryptophane Soluble at Neutral pH.,The Journal of Organic Chemistry

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Selective Capture of Thallium and Cesium by a Cryptophane Soluble at Neutral pH.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-06-26 , DOI: 10.1021/acs.joc.0c00950
Thierry Brotin ₁ , Patrick Berthault ₂ , Delphine Pitrat ₁ , Jean-Christophe Mulatier ₁

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We report in this article the synthesis of an asymmetrical cryptophane derivative (possessing only C₃-symmetry) bearing three phenol groups and three other carboxylic acid functions, each of these groups on the aromatic rings. Thanks to isothermal titration calorimetry experiments, we show that this compound binds large monovalent cations, such as Cs⁺ and Tl⁺, with a binding constant significantly lower than its congeners bearing a larger number of phenol groups grafted on the benzene rings. However, higher selectivity for Cs⁺ and Tl⁺ was observed with this compound since it does not show any affinity for other alkali cations. More importantly, due to the greater solubility of this derivative in pure water, we show for the first time that effective thallium(I) complexation takes place at neutral pH. This result demonstrates that cryptophane derivatives decorated with a higher number of phenol groups are promising host molecules for removing traces of thallium(I) from aqueous phases at neutral pH or above.

中文翻译：

色氨酸在中性pH下可选择性捕获Capture和铯。

我们在本文中报道了带有三个酚基团和三个其他羧酸官能团（芳香族环上每个基团）的不对称隐烷衍生物的合成（仅具有C _3-对称性）。通过等温滴定量热法实验，我们表明该化合物结合大的单价阳离子（例如Cs ⁺和Tl ^+），其结合常数明显低于其带有接枝在苯环上的大量酚基团的同类物。但是，对Cs ⁺和Tl ^+的选择性更高由于该化合物对其他碱性阳离子没有任何亲和力，因此观察到该化合物。更重要的是，由于该衍生物在纯水中的溶解度更高，我们首次证明有效的th（I）络合在中性pH下发生。该结果表明，装饰有大量酚基的隐色烷衍生物是有希望的宿主分子，用于在中性pH或更高的pH条件下从水相中去除痕量的（（I）。

更新日期：2020-08-08

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