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

作　　者：Hui Wang Zhi-Jun Zhang Heng-Yi Zhang Yu Liu 

机构地区：[1]Department of Chemistry,State Key Laboratory of Elemento-Organic Chemistry,Nankai University

出　　处：《Chinese Chemical Letters》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

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 guest 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 guest 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.

关 键 词：Rotaxane Crown ether Charger transfer （CT） Click chemistry 

分 类 号：O621.3[理学—有机化学]