Synthetic receptor which uses multiple edge-face interactions to bind aromatic guests

被引:40
作者
Cloninger, MJ [1 ]
Whitlock, HW [1 ]
机构
[1] Univ Wisconsin, Dept Chem, SM Mcelvain Labs Organ Chem, Madison, WI 53706 USA
关键词
D O I
10.1021/jo980193x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Host 1 binds bicyclic aromatic guests such as 6-nitro-2-naphthol 2, serotonin mimic 3, and stilbene-derivative 4 with high affinity. Competition studies were performed to determine the association constants for complexation of 2-4 by 1. Lower-affinity host 14 lacked the structural requirements to form edge-face contacts with guests 2-4 and served as the competitive host. For each guest, evaluation of the geometry of the host-guest interaction by low-temperature NMR experiments revealed two edge-face interactions between the face of the anthracene bridge of 1 and the edge of the guest. The results reported in this paper suggest that the observed edge-face interactions stabilize the complexes formed by host 1. The synthesis of host 1 and the complexation of 2-4 by this host are described.
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页码:6153 / 6159
页数:7
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