Click chemistry between Nitrile N-Oxide and alkyne for polyrotaxanes

Macromolecules, DOI: 10.1021/ma100262g First published: April 2, 2010 Toshikazu Takata et al.

Click chemistry is more than alkyne-azide reaction - this article demonstrates a click chemistry using unstable and stable homoditopic nitrile N-oxides. Nitrile N-oxide was generated in situ through the reaction of the corresponding hydroxamoyl chloride with 4-Angstrom molecular sieves and was subjected to click reaction with alkynes. A kinetically stabilized homoditopic nitrile N-oxide was also developed for the same purpose. 

Polyrotaxane, a new class of polymer characterized by the mechanical linkage of its components, shows unique physical, chemical, mechanical, and rheological properties. Preparation of these sophisticated supramolecular systems requires powerful, highly reliable, and selective reactions. The above click chemistry is applied for the preparation of main-chain-type polyrotaxanes. The rotaxanation - polymerization by this click chemistry provides remarkable advantage of avoidance of catalyst contamination which exists in alkyne-azide click chemistry.

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