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Wu, Yong; Guo, Qing-Hui; Qiu, Yunyan; Weber, Jacob A.; Young, Ryan M.; Bancroft, Laura; Jiao, Yang; Chen, Hongliang; Song, Bo; Liu, Wenqi; et al (, Proceedings of the National Academy of Sciences)Although catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, we report the design and syntheses of two 3D catenanes by a sequence of S N 2 reactions in one pot. The resulting triply mechanically interlocked molecules were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold symmetric cage component as the suit and a tribromide component as the body, is formed at elevated temperatures. This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodynamic minima. We foresee a future in which this particular synthetic strategy guides the rational design and production of mechanically interlocked molecules under kinetic control.more » « less
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Guo, Qing-Hui; Zhou, Jiawang; Mao, Haochuan; Qiu, Yunyan; Nguyen, Minh T.; Feng, Yuanning; Liang, Jiaqi; Shen, Dengke; Li, Penghao; Liu, Zhichang; et al (, Journal of the American Chemical Society)
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Varni, Anthony J.; Fortney, Andria; Baker, Matthew A.; Worch, Joshua C.; Qiu, Yunyan; Yaron, David; Bernhard, Stefan; Noonan, Kevin J.; Kowalewski, Tomasz (, Journal of the American Chemical Society)
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Cai, Kang; Mao, Haochuan; Liu, Wei-Guang; Qiu, Yunyan; Shi, Yi; Zhang, Long; Shen, Dengke; Chen, Hongliang; Jiao, Yang; Wu, Huang; et al (, Journal of the American Chemical Society)
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