Efficient potassium-ion-templated synthesis and controlled destruction of [2]rotaxanes based on cascade complexes

被引:28
作者
Han, Tao [1 ,2 ]
Chen, Chuan-Feng [1 ]
机构
[1] Chinese Acad Sci, Inst Chem, Ctr Chem Biol, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1021/jo801522f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The triptycene-based macrotricyclic host can form pseudorotaxane-like cascade complexes with anthraquinone and its tetra-azide terminally functionalized derivative in the presence of potassium ions, which subsequently resulted in the synthesis of three novel potassium-ion-templated [2]rotaxanes 10-12 in high yields by the "threading followed by stoppering" approach. Since the potassium ions act not only as templates during the stoppering reactions but also as nonslipping chocks to shrink the inner diameter of the wheel cavity, the deslipping behaviors of the [2]rotaxanes with different triazole stoppers by peeling off the potassium ions with 18-crown-6 were further investigated. The results show that rotaxanes 10 and 11 can be destroyed, but under the same conditions the dumbbell and ring components of rotaxane 12 remain interlocked.
引用
收藏
页码:7735 / 7742
页数:8
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