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Self-Assembly of Stimuli-Responsive [2]Rotaxanes by Amidinium Exchange
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2021-09-24 , DOI: 10.1021/jacs.1c05230 Oleg Borodin 1 , Yevhenii Shchukin 1 , Craig C Robertson 2 , Stefan Richter 1 , Max von Delius 1
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2021-09-24 , DOI: 10.1021/jacs.1c05230 Oleg Borodin 1 , Yevhenii Shchukin 1 , Craig C Robertson 2 , Stefan Richter 1 , Max von Delius 1
Affiliation
Advances in supramolecular chemistry are often underpinned by the development of fundamental building blocks and methods enabling their interconversion. In this work, we report the use of an underexplored dynamic covalent reaction for the synthesis of stimuli-responsive [2]rotaxanes. The formamidinium moiety lies at the heart of these mechanically interlocked architectures, because it enables both dynamic covalent exchange and the binding of simple crown ethers. We demonstrated that the rotaxane self-assembly follows a unique reaction pathway and that the complex interplay between crown ether and thread can be controlled in a transient fashion by addition of base and fuel acid. Dynamic combinatorial libraries, when exposed to diverse nucleophiles, revealed a profound stabilizing effect of the mechanical bond as well as intriguing reactivity differences between seemingly similar [2]rotaxanes.
中文翻译:
通过脒交换自组装刺激响应 [2] 轮烷
超分子化学的进步通常以开发能够实现它们相互转化的基本构件和方法为基础。在这项工作中,我们报告了使用未充分探索的动态共价反应合成刺激响应的 [2] 轮烷。甲脒部分位于这些机械联锁结构的核心,因为它能够实现动态共价交换和简单冠醚的结合。我们证明了轮烷自组装遵循独特的反应途径,并且可以通过添加碱和燃料酸以瞬时方式控制冠醚和线之间的复杂相互作用。动态组合库,当暴露于不同的亲核试剂时,
更新日期:2021-10-13
中文翻译:
通过脒交换自组装刺激响应 [2] 轮烷
超分子化学的进步通常以开发能够实现它们相互转化的基本构件和方法为基础。在这项工作中,我们报告了使用未充分探索的动态共价反应合成刺激响应的 [2] 轮烷。甲脒部分位于这些机械联锁结构的核心,因为它能够实现动态共价交换和简单冠醚的结合。我们证明了轮烷自组装遵循独特的反应途径,并且可以通过添加碱和燃料酸以瞬时方式控制冠醚和线之间的复杂相互作用。动态组合库,当暴露于不同的亲核试剂时,