Synthesis of a bistable [3]rotaxane and its pH-controlled intramolecular charge-transfer behavior


A [3]rotaxane 1 involving two naphtho-21-crown-7 (N21C7) rings and a dumbbell-shaped component 4 was synthesized. The dumbbell-shape molecule 4 contains one viologen nucleus, two secondary alkyl ammonium sites and two phenyl stoppers. After threading the N21C7 ring with the thread-like ammonium guest 3, the copper(I)-catalyzed Huisgen alkyne-azide 1,3-dipolar cycloaddition (CuAAC ‘‘click’’ reaction), was performed to connect the pseudorotaxanes with viologen unit 2 and generate 1. Through treating the [3]rotaxane by the base and acid circularly, the twoN21C7 rings canmake shuttling motion along the axle. Meanwhile the distance between the electron-deficient viologen unit and the electron-rich naphthol group can be adjusted precisely along with a remarkable intramolecular chargetransfer (CT) behavior. 2013 Yu Liu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

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@inproceedings{Wang2013SynthesisOA, title={Synthesis of a bistable [3]rotaxane and its pH-controlled intramolecular charge-transfer behavior}, author={Hui Wang and Zhijun Zhang and Hengyi Zhang and Yu Liu}, year={2013} }