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

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Abstract 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.

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