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A Six‐Crossing Doubly Interlocked [2]Catenane with Twisted Rings, and a Molecular Granny Knot
Author(s) -
Da Jonathan J.,
Leigh David A.,
Pisano Simone,
Valero Alberto,
VitoricaYrezabal Iñigo J.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807135
Subject(s) - catenane , knot (papermaking) , chemistry , olefin metathesis , stereochemistry , trefoil knot , crystallography , metathesis , molecule , knot theory , materials science , polymerization , organic chemistry , composite material , polymer
A molecular 6 23link (a six crossing, doubly interlocked, [2]catenane with twisted rings) and a 3 1 #3 1 granny knot (a composite knot made up of two trefoil tangles of the same handedness) were constructed by ring‐closing olefin metathesis of an iron(II)‐coordinated 2×2 interwoven grid. The connections were directed by pendant phenyl groups to be between proximal ligand ends on the same faces of the grid. The 6 23link was separated from the topoisomeric granny knot by recycling size‐exclusion chromatography. The identity of each topoisomer was determined by tandem mass spectrometry and the structure of the 6 23link confirmed by X‐ray crystallography, which revealed two 82‐membered macrocycles, each in figure‐of‐eight conformations, linked through both pairs of loops.