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A Cyclic RotaxaneContributor(s):Timothy M. Swager, Birgit Esser
Université de Strasbourg, France and UniVersity of Jyväskylä, Finland
Templated Synthesis of Cyclic Rotaxanes Consisting of Two Stiff Rods Threaded through Two Bis-macrocycles with a Large and Rigid Central Plate as Spacer
J. Am. Chem. Soc. 2010, 132: 6840-6850
22 July 2010 (online)
rotaxanes - click chemistry - macrocycles
The authors synthesized the two cyclic rotaxanes 1 and 2. The structure of 2, containing zinc porphyrin units, was determined by X-ray crystallography and is the largest rotaxane molecule characterized in this way.
The synthetic strategy includes the quantitative copper-driven assembly and threading of 5 through the macrocycles 3,4 and the attachment of stoppers 8 by click chemistry in high yields. Compound 2 was tested as a receptor for ditopic guests in complexation studies.