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A Strategy Utilizing a Recyclable Macrocycle Transporter for the Efficient Synthesis of a Triazolium‐Based [2]Rotaxane
Author(s) -
Chao Sovy,
Romuald Camille,
FournelMarotte Karine,
Clavel Caroline,
Coutrot Frédéric
Publication year - 2014
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.201403765
Subject(s) - rotaxane , moiety , chemistry , slippage , sequence (biology) , transporter , yield (engineering) , stereochemistry , combinatorial chemistry , materials science , molecule , organic chemistry , biochemistry , supramolecular chemistry , gene , composite material , metallurgy
A general synthesis of triazolium‐containing [2]rotaxanes, which could not be accessed by other methods, is reported. It is based on a sequential strategy starting from a well‐designed macrocycle transporter which contains a template for dibenzo‐24‐crown‐8 and a N ‐hydroxysuccinimide (NHS) moiety. The sequence is: 1) synthesis by slippage of a [2]rotaxane building‐block; 2) its elongation at its NHS end; 3) the delivery of the macrocycle to the elongated part of the axle by an induced translational motion; 4) the contraction process to yield the targeted [2]rotaxane and recycle the initial transporter.