Translational isomerism in some two- and three-station [2]rotaxanes

被引:21
作者
Amabilino, DB [1 ]
Ashton, PR [1 ]
Boyd, SE [1 ]
GomezLopez, M [1 ]
Hayes, W [1 ]
Stoddart, JF [1 ]
机构
[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND
关键词
D O I
10.1021/jo9612584
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The template-directed syntheses of three [2]rotaxanes are described. They all have dumbbell components, with both hydroquinone and resorcinol rings inserted into polyether chains terminated by tetraarylmethane stoppers, that become encircled during the key self-assembly processes by the tetracationic cyclophane, cyclobis(paraquat-p-phenylene), with its two pi-electron deficient bipyridinium units. It has been demonstrated by low-temperature H-1 NMR spectroscopy that the pi-electron deficient tetracationic cyclophane has a remarkably high preference to reside around the hydroquinone ring in these molecular shuttles. This observation illustrates how a very small constitutional difference-hydroquinone versus resorcinol recognition sites-can lead to the overwhelming preference for one translational isomer over another in this particular range of [2]rotaxanes.
引用
收藏
页码:3062 / 3075
页数:14
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