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De Novo Construction of Catenanes with Dissymmetric Cages by Space‐Discriminative Post‐Assembly Modification
Author(s) -
Li Pan,
Xu Shijun,
Yu Chunyang,
Li ZiYing,
Xu Jianping,
Li ZiMu,
Zou Lingyi,
Leng Xuebing,
Gao Shan,
Liu Zhiqiang,
Liu Xiaoyun,
Zhang Shaodong
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202000442
Subject(s) - catenane , catenation , molecule , topology (electrical circuits) , chemistry , crystallography , nanotechnology , materials science , mathematics , combinatorics , organic chemistry , dna , biochemistry
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.