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Knotaxanes—Rotaxanes with Knots as Stoppers

✍ Scribed by Oleg Lukin; Takateru Kubota; Yoshio Okamoto; Frauke Schelhase; Albena Yoneva; Walter M. Müller; Ute Müller; Fritz Vögtle

Publisher
John Wiley and Sons
Year
2003
Tongue
English
Weight
161 KB
Volume
42
Category
Article
ISSN
0044-8249

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✦ Synopsis

Dedicated to Professor Karl Heinz Dötz on the occasion of his 60th birthday

In a recent report [1] we coined the name "knotaxane" for a challenging, yet hitherto unknown, hypothetical type of compound: a rotaxane in which the stoppers are molecular knots. Here we report the first successful synthesis of two members of this new topological family and their chiral resolution. Interest in this species comes on the one hand from their topological chirality, [2] since unlike having just a stereocenter, as in classical stereochemistry, the whole nanosized molecular skeleton is chiral ("nanochiral"). Their chirality, therefore, should be quite pronounced, [3] and strong chiroptic effects and chiral inductions are expected. The use of the rotaxane platform, [2,4,5] on the other hand, makes such an assembly a particularly attractive architecture with an option to control the direction [6] of rotation or the shuttling [4c] of mechanically linked constituent parts.

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In this paper we report on amide rotaxanes with achiral wheels 2a and 2b and chiral axle indicate intermolecular host-guest interactions, likewise. After an tetrabenzoylglucose stoppers. When acetyl groups are used instead of benzoyl groups, merely a pseudo-rotaxane 5 is addition of a solution of Na

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## Abstract The new π‐donor/π‐acceptor type rotaxanes 15, 16 bearing chiral sugar units as blocking groups have been synthesized in 2% and 6% yield, starting from acetobromo glucose 10 and the podands 8 or 9, followed by the reaction of the resulting axles 11 and 12 with the dicationic bis(bipyridi