合成具有全氟烷基硫代苄基作为高活性卤化物受体的斑蝥素

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Matúš Chvojka, Hennie Valkenier and Vladimír Šindelář
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引用次数: 0

摘要

制备具有超高结合亲和力的阴离子受体是超分子化学的一个重要而又具有挑战性的课题。因此,寻找能提高阴离子受体性能的新结构基团是一项重要任务。在此背景下,我们报告了新型氟化斑[6]脲的合成过程,这些斑[6]脲含有独特的苄基取代基和全氟化烷硫基,旨在增强其阴离子受体能力。所开发的合成策略可以高效地制备这些结构基团。利用 19F NMR 竞争实验观察和量化了卤化物与所制备的 bambus[6]urils 之间复合物的超高稳定性。用 SCF3 基团取代苯甲酰化班布斯[6]脲上的 CF3 基团,增加了大环对阴离子的亲和力,并提供了有报道以来最强的碘受体,在乙腈中的结合亲和力为 4-1013 M-1。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors†

Synthesis of bambusurils with perfluoroalkylthiobenzyl groups as highly potent halide receptors†

The preparation of anion receptors with ultrahigh binding affinities is an important, yet challenging, topic of supramolecular chemistry. The search for new structural motifs which would enhance the performance of anion receptors is therefore an important task. In this context, we report the synthesis of novel fluorinated bambus[6]urils that incorporate unique benzyl substituents with perfluoroalkylthio groups, aimed at enhancing their anion receptor capabilities. The synthetic strategy developed allows for the efficient preparation of these structural motifs. Ultrahigh stability of the complexes between halides and the prepared bambus[6]urils was observed and quantified using 19F NMR competition experiments. Replacing –CF3 groups on benzylated bambus[6]urils by –SCF3 groups increased the affinity of the macrocycles towards anions and provided the strongest iodide receptor reported with a binding affinity of 4 × 1013 M−1 in acetonitrile.

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来源期刊
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
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