Directional Shuttling of a Stimuli‐Responsive Cone‐Like Macrocycle on a Single‐State Symmetric Dumbbell Axle

Rotaxane‐based molecular shuttles are often operated using low‐symmetry axles and changing the states of the binding stations. A molecular shuttle capable of directional shuttling of an acid‐responsive cone‐like macrocycle on a single‐state symmetric dumbbell axle is now presented. The axle contains...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-06, Vol.57 (26), p.7809-7814
Main Authors: Cui, Jie‐Shun, Ba, Qian‐Kai, Ke, Hua, Valkonen, Arto, Rissanen, Kari, Jiang, Wei
Format: Article
Language:English
Subjects:
Acids
Ammonium
Binding
host–guest chemistry
macrocycles
Molecular chains
Molecular machines
rotaxanes
Shafts (machine elements)
Stations
supramolecular chemistry
Symmetry
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Summary:Rotaxane‐based molecular shuttles are often operated using low‐symmetry axles and changing the states of the binding stations. A molecular shuttle capable of directional shuttling of an acid‐responsive cone‐like macrocycle on a single‐state symmetric dumbbell axle is now presented. The axle contains three binding stations: one symmetric di(quaternary ammonium) station and two nonsymmetric phenyl triazole stations arranged in opposite orientations. Upon addition of an acid, the protonated macrocycle shuttles from the di(quaternary ammonium) station to the phenyl triazole binding station closer to its butyl groups. This directional shuttling presumably originates from charge repulsion and an orientational binding preference between the cone‐like cavity and the nonsymmetric phenyl triazole station. This mechanism for achieving directional shuttling by manipulating only the wheels instead of the tracks is new for artificial molecular machines. Directional shuttling was achieved with an acid‐responsive cone‐like macrocycle on a single‐state symmetric dumbbell axle due to charge repulsion and the orientational binding preference of the macrocycle for the nonsymmetric binding station. This operating mechanism, involving manipulating wheels instead of tracks, is new for artificial molecular machines.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201803349