Zwitterion detection with a fluorescent squaramide cryptand: a study on size-dependent salt recognition and sensing,Organic Chemistry Frontiers

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Zwitterion detection with a fluorescent squaramide cryptand: a study on size-dependent salt recognition and sensing
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-07-09 , DOI: 10.1039/d4qo01136h
Marta Zaleskaya-Hernik ₁ , Marcin Wilczek ₁ , Łukasz Dobrzycki ₁ , Jan Romański ₁

Affiliation

We report the synthesis of a novel squaramide-based cryptand incorporating both anion and cation binding domains, and a fluorescent reporter designed to monitor the complexation process. The preorganization of the binding domains in the cryptand structure favored stronger binding of anions as compared with the open chain counterpart. X-ray structural analysis of the cryptand complex with ion pairs confirmed the interaction of ions with binding sites in the solid state. Employing a ball milling technique resolved solubility issues, facilitating the study of interactions between the cryptand and salts. We found that the cryptand exhibits stronger binding affinity for carboxylates than for chloride anions. This property, coupled with the closed structure of the cryptand, was utilized for the selective recognition of zwitterions differing in chain length. Mechanochemical methods allow for qualitative binding of amino acids within the receptor cavity. Fluorescence studies revealed the behavior of cryptand 1 as a sensor enabling the selective recognition of zwitterions, a capability not observed in the sensors with an open structure.

中文翻译：

使用荧光方酰胺穴状配体进行两性离子检测：尺寸依赖性盐识别和传感的研究

我们报告了一种新型的基于方酰胺的穴状配体的合成，该穴状配体结合了阴离子和阳离子结合域，以及旨在监测络合过程的荧光报告基因。与开链对应物相比，穴状配体结构中结合结构域的预组织有利于更强的阴离子结合。带有离子对的穴状配体复合物的 X 射线结构分析证实了离子与固态结合位点的相互作用。采用球磨技术解决了溶解度问题，促进了穴状配体和盐之间相互作用的研究。我们发现穴状配体对羧酸盐的结合亲和力比对氯阴离子的结合亲和力更强。该特性与穴状配体的封闭结构相结合，用于选择性识别链长不同的两性离子。机械化学方法允许受体腔内氨基酸的定性结合。荧光研究揭示了 cryptand 1 作为传感器的行为，能够选择性识别两性离子，而开放结构的传感器中未观察到这种能力。

更新日期：2024-07-09

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