An Octacationic [2]Catenane Formed by Oxime Condensation: A Bistable Molecular Switch,ChemPlusChem

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An Octacationic [2]Catenane Formed by Oxime Condensation: A Bistable Molecular Switch
ChemPlusChem ( IF 3.0 ) Pub Date : 2019-11-20 , DOI: 10.1002/cplu.201900668
Cai‐Yun Wang ₁ , Guangcheng Wu ₁ , Jiaqi Zhu ₁ , Tianyu Jiao ₁ , Yang Zhang ₁ , Hao Li ₁

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Oxime condensation as well as template‐directed synthesis based on radical‐pairing interactions were used in the synthesis of an octacationic [2]catenane in 20 % yield. The [2]catenane consists of two identical mechanically interlocked tetracationic macrocyclic components. Each of the ring components contains two dicationic bipyridinium (BIPY²⁺) functions. The structure of the [2]catenane was fully characterized by NMR spectroscopy, mass spectrometry, as well as X‐ray crystallography. In the oxidized state, the [2]catenane exists in a co‐conformation where its four BIPY²⁺ units are located as far as possible from each other. Upon reduction of BIPY²⁺ into the radical state, namely BIPY^+., we propose that the [2]catenane undergoes mechanical movement, driven by radical pairing interactions between these radical building blocks. The redox‐stimulated switching behavior of this [2]catenane was confirmed by electrochemistry, UV‐Vis‐NIR absorption spectroscopy, and ¹H NMR spectroscopy.

中文翻译：

肟缩合形成的八[2]癸烷：双稳态分子开关。

肟缩合以及基于自由基配对相互作用的模板指导的合成反应以20％的产率用于合成辛酸[2]环烷。[2] catenane由两个相同的机械互锁的四阳离子大环组分组成。每个环成分都包含两个双联吡啶鎓（BIPY ²⁺）功能。[2]联烷的结构已通过NMR光谱，质谱和X射线晶体学进行了全面表征。在氧化状态下，[2]联烷以共构形式存在，其四个BIPY ²⁺单元尽可能地彼此位于同一位置。当BIPY ²⁺还原为自由基状态时，即BIPY ^+。，我们建议[2]环烷经历机械运动，由这些自由基构件之间的自由基配对相互作用驱动。通过电化学，UV-Vis-NIR吸收光谱和¹ H NMR光谱证实了这种[2]联烷的氧化还原刺激的转换行为。

更新日期：2019-11-20

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