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A Tetrameric Cage with D 2 h Symmetry through Alkyne Metathesis
Author(s) -
Wang Qi,
Zhang Chenxi,
Noll Bruce C.,
Long Hai,
Jin Yinghua,
Zhang Wei
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404880
Subject(s) - cage , metathesis , chemistry , alkyne , covalent bond , crystallography , stereochemistry , salt metathesis reaction , dynamic covalent chemistry , catalysis , crystal structure , polymerization , organic chemistry , supramolecular chemistry , polymer , combinatorics , mathematics
Abstract Shape‐persistent covalent organic polyhedrons (COPs) with ethynylene linkers are usually prepared through kinetically controlled cross‐coupling reactions. The high‐yielding synthesis of ethynylene‐linked rigid tetrameric cages via one‐step alkyne metathesis from readily accessible triyne precursors is presented. The tetrameric cage contains two macrocyclic panels and exhibits D 2 h symmetry. The assembly of such a COP is a thermodynamically controlled process, which involves the initial formation of macrocycles as key intermediates followed by the connection of two macrocycles with ethynylene linkages. With a large internal cavity, the cage exhibits a high binding selectivity toward C 70 ( K= 3.9×10 3  L mol −1 ) over C 60 (no noticeable binding).

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