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Synfacts 2010(8): 0891-0891
DOI: 10.1055/s-0030-1257834
DOI: 10.1055/s-0030-1257834
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
A Cyclic [4]Rotaxane
Contributor(s):Timothy M. Swager, Birgit EsserJ.-P. Collin*, F. Durola, J. Frey, V. Heitz*, F. Reviriego, J.-P. Sauvage*, Y. Trolez, K. Rissanen*
Université de Strasbourg, France and UniVersity of Jyväskylä, Finland
Templated Synthesis of Cyclic [4]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
Université de Strasbourg, France and UniVersity of Jyväskylä, Finland
Templated Synthesis of Cyclic [4]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
Further Information
Publication History
Publication Date:
22 July 2010 (online)
Key words
rotaxanes - click chemistry - macrocycles
Significance
The authors synthesized the two cyclic [4]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.
Comment
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.