De Novo Construction of Catenanes with Dissymmetric Cages by Space-Discriminative Post-Assembly Modification |
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| Authors: | Dr. Pan Li Shijun Xu Prof. Chunyang Yu Zi-Ying Li Jianping Xu Zi-Mu Li Lingyi Zou Dr. Xuebing Leng Shan Gao Prof. Zhiqiang Liu Prof. Xiaoyun Liu Prof. Shaodong Zhang |
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| Affiliation: | 1. Frontiers Science Center for Transformative Molecules, Shanghai Key Laboratory of Electrical Insulation and Thermal Aging, School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai, 200240 China;2. Key Laboratory of Specially Functional Polymeric Materials and Related Technology (ECUST), Ministry of Education, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237 China;3. State Key Laboratory of Organometallic Chemistry, Shanghai, Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China;4. Neurological Department, Shanghai Jiao Tong University Affiliated Sixth People's Hospital, South Campus, Shanghai, 200240 China;5. The National and Local Joint Engineering Research Center for Biomanufacturing of Chiral Chemicals, Zhejiang University of Technology, Hangzhou, 310014 China |
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| Abstract: | Considerable efforts have been made to increase the topological complexity of mechanically interlocked molecules over the years. Three-dimensional catenated structures composed of two or several (usually symmetrical) cages are one representative example. However, owing to the lack of an efficient universal synthetic strategy, interlocked structures made up of dissymmetric cages are relatively rare. Since the space volume of the inner cavity of an interlocked structure is smaller than that outside it, we developed a novel synthetic approach with the voluminous reductant NaBH(OAc)3 that discriminates this space difference, and therefore selectively reduces the outer surface of a catenated dimer composed of two symmetric cages, thus yielding the corresponding catenane with dissymmetric cages. Insight into the template effect that facilitates the catenation of cages was provided by computational and experimental techniques. |
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| Keywords: | Catenane Verzahnte Käfige Reduktionen Strukturtopologie Supramolekulare Chemie |
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