Self-Assembled Cage-like Receptor that Binds Biologically Relevant Dicarboxylic Acids via Proton Coupled Anion Recognition,Journal of the American Chemical Society

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Self-Assembled Cage-like Receptor that Binds Biologically Relevant Dicarboxylic Acids via Proton Coupled Anion Recognition
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2020-01-02 , DOI: 10.1021/jacs.9b11566
Fei Wang , Sajal Sen ₁ , Chuang Chen , Steffen Bähring ₂ , Chuanhu Lei , Zhiming Duan , Zhan Zhang ₃ , Jonathan L Sessler ₁ , Atanu Jana

Affiliation

We report here a fully organic, self-assembled dimeric receptor, constructed from acyclic naphthyridylpolypyrrolic building block. The cage-like dimer is stable in the solid state, in solution, and in gas phase, as inferred from X-ray diffraction, and spectroscopic analyses. This system acts as a receptor for oxalic acid, maleic acid, and malonic acid in the solid state and in THF solution. In contrast, acetic acid, propionic acid, adipic acid and succinic acid, with pKa values  ca. 2.8, were not bound effectively within the cage-like cavity. It is speculated that oxalic acid, maleic acid, and malonic acid serve to proto-nate the naphthyridine moieties of the host, which then favors binding of the corresponding carboxylate anions via hydrogen-bonding to the pyrrolic NH protons. The present naphthyridinepolypyrrole dimer is stable under acidic conditions, includ-ing in the presence of 100 equiv trifluoroacetic acid (TFA), para-toluenesulfonic acid (PTSA), H2SO4, and HCl. However, disassembly may be achieved by exposure to tetrabutylammonium fluoride (TBAF). Washing with water then regenerates the cage. This process of assembly and disassembly could be repeated ≥20 times with little evidence of degradation. The reversible nature of the present system, coupled with its dicarboxylic acid recognition features, leads us to suggest it could have a role to play in effecting the controlled 'capture' and 'release' of biologically relevant dicarboxylic acids.

中文翻译：

通过质子偶联阴离子识别结合生物相关二羧酸的自组装笼状受体

我们在这里报告了一种完全有机的、自组装的二聚体受体，由无环萘啶-聚吡咯构建块构建。根据 X 射线衍射和光谱分析推断，笼状二聚体在固态、溶液和气相中都是稳定的。该系统充当草酸、马来酸和丙二酸在固态和四氢呋喃溶液中的受体。相比之下，乙酸、丙酸、己二酸和琥珀酸的 pKa 值  ca。2.8，未在笼状腔内有效结合。据推测，草酸、马来酸和丙二酸用于使宿主的萘啶部分质子化，然后通过氢键与吡咯 NH 质子结合相应的羧酸根阴离子。本发明的萘啶-聚吡咯二聚体在酸性条件下是稳定的，包括在 100 当量的三氟乙酸 (TFA)、对甲苯磺酸 (PTSA)、H2SO4 和 HCl 存在下。然而，可以通过暴露于四丁基氟化铵 (TBAF) 来实现分解。然后用水洗涤使笼子再生。这种组装和拆卸过程可以重复≥20 次，几乎没有退化迹象。本系统的可逆性质，加上其二羧酸识别特征，使我们认为它可能在影响生物相关二羧酸的受控“捕获”和“释放”方面发挥作用。可通过暴露于四丁基氟化铵 (TBAF) 来实现分解。然后用水洗涤使笼子再生。这种组装和拆卸过程可以重复≥20 次，几乎没有退化迹象。本系统的可逆性质，加上其二羧酸识别特征，使我们认为它可能在影响生物相关二羧酸的受控“捕获”和“释放”方面发挥作用。可通过暴露于四丁基氟化铵 (TBAF) 来实现分解。然后用水洗涤使笼子再生。这种组装和拆卸过程可以重复≥20 次，几乎没有退化迹象。本系统的可逆性质，加上其二羧酸识别特征，使我们认为它可能在影响生物相关二羧酸的受控“捕获”和“释放”方面发挥作用。

更新日期：2020-01-02

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