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Synthesis and Binding Properties of Monohydroxycucurbit[7]uril: A Key Derivative for the Functionalization of Cucurbituril Hosts

机译:单羟基毛细血管的合成及结合性质[7] URIL:葫芦菌核官能化的关键衍生物

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摘要

We present a simple, direct method to prepare monohydroxylated cucurbit[7]uril (CB7-OH) through the direct oxidation of its precursor host, cucurbit[7]uril (CB7). Although the conversion takes place in low yield (14%), the isolation of CB7-OH from the reaction mixture is straightforward, and the unreacted CB7 can be easily recovered. ITC measurements with several selected guests confirmed that CB7-OH binds all of them in aqueous solution with similar, albeit slightly lower, binding affinities than those observed with the unmodified CB7 host. ESI mass spectrometric competition experiments are consistent with the ITC measurements. A variety of spectroscopic and voltammetric measurements also verify that the CB7-OH complexes exhibit properties essentially identical to those of the CB7 complexes. DFT computational data also confirm the similar thermodynamic stabilities and structures of the CB7-OH and CB7 inclusion complexes. Finally, the high thermodynamic stability of the CB7-OH complexes was used to improve on the extraction efficiency of stir bar sorptive extraction methods after suitable modification of the active coating with CB7-OH.
机译:我们呈现了一种简单,直接的方法,通过其前体宿主的直接氧化来制备单羟基化葫芦[7] URIL(CB7-OH),葫芦(CB7)。虽然转化率以低产率(14%)进行,但是从反应混合物中分离CB7-OH是直的,并且可以容易地回收未反应的CB7。具有几个选定的客人的ITC测量证实CB7-OH将所有它们在水溶液中与略低,结合亲和力的含量略低,而不是用未修饰的CB7宿主观察到的那些。 ESI质谱竞争实验与ITC测量一致。各种光谱和伏安测量还验证CB7-OH复合物表现出与CB7复合物的特性相同的性质。 DFT计算数据还证实了CB7-OH和CB7包合物的类似热力学稳定性和结构。最后,使用CB7-OH络合物的高热力学稳定性来改善搅拌棒吸附萃取方法的萃取效率,得到CB7-OH的活性涂层后的搅拌棒吸附萃取方法。

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  • 来源
    《The Journal of Organic Chemistry》 |2018年第10期|共7页
  • 作者单位

    School of Chemistry and Chemical Engineering Guizhou University Guiyang 550025 China;

    School of Chemistry and Chemical Engineering Guizhou University Guiyang 550025 China;

    School of Chemistry and Chemical Engineering Guizhou University Guiyang 550025 China;

    Department of Chemistry University of Miami Coral Gables Florida 33124-0431 United States;

    Department of Chemistry University of Miami Coral Gables Florida 33124-0431 United States;

    Department of Chemistry University of Miami Coral Gables Florida 33124-0431 United States;

    Department of Chemistry University of Miami Coral Gables Florida 33124-0431 United States;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
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