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Synthesis of a bistable[3]rotaxane and its pH-controlled intramolecular charge-transfer behavior 被引量:6

Synthesis of a bistable[3]rotaxane and its pH-controlled intramolecular charge-transfer behavior
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摘要 A [3]rotaxane I involving two naphtho-21-crown-7 (N21 C7) 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 vip 3, the copper(l)-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 two N21 C7 rings can make 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 charge- transfer (CT) behavior. A [3]rotaxane I involving two naphtho-21-crown-7 (N21 C7) 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 vip 3, the copper(l)-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 two N21 C7 rings can make 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 charge- transfer (CT) behavior.
出处 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第7期563-567,共5页 中国化学快报(英文版)
基金 the National Basic Research Program of China(973 Program,No.2011CB932500) the National Natural Science Foundation of China(Nos.20932004 and 20972077) for financial support
关键词 Rotaxane Crown ether Charger transfer (CT) Click chemistry Rotaxane Crown ether Charger transfer (CT) Click chemistry
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