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Cyclodextrin Rotaxane with Switchable Pirouetting.

ABSTRACT: A [1]rotaxane with two threaded ?-cyclodextrin (?-CD) wheels was synthesized in 92% yield using a one-pot process at room temperature that employed spontaneous ?-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded ?-CD wheels around the encapsulated dumbbell was switched "ON" or "OFF" by the presence of chemical additives that controlled boronate ester bond formation between the interlocked components.

SUBMITTER: Zhang QW 

PROVIDER: S-EPMC5904832 | biostudies-literature | 2018 Apr

REPOSITORIES: biostudies-literature

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Cyclodextrin Rotaxane with Switchable Pirouetting.

Zhang Qi-Wei QW   Zajíček Jaroslav J   Smith Bradley D BD  

Organic letters 20180315 7

A [1]rotaxane with two threaded α-cyclodextrin (α-CD) wheels was synthesized in 92% yield using a one-pot process at room temperature that employed spontaneous α-CD threading onto a 12-carbon alkyl chain in water followed by an oxime condensation reaction that attached two boronic acid-containing stopper groups. Rapid pirouetting of the threaded α-CD wheels around the encapsulated dumbbell was switched "ON" or "OFF" by the presence of chemical additives that controlled boronate ester bond format  ...[more]

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