First pseudorotaxane-like [3]complexes based on cryptands and paraquat: Self-assembly and crystal structures

被引:139
作者
Huang, FH
Gibson, HW [1 ]
Bryant, WS
Nagvekar, DS
Fronczek, FR
机构
[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA
[2] Louisiana State Univ, Dept Chem, Baton Rouge, LA 70803 USA
关键词
D O I
10.1021/ja034968h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new cryptand, bis(1,3,5-phenylene)tri(1,4,7,10-tetraoxadecyl) (3a), has been synthesized in good yield from bis(5-hydroxy-1,3-phenylene)-26-crown-8 (2a) and tri(ethylene glycol) ditosylate using pseudo-high dilution conditions. 3a forms a strong 1:1 complex with paraquat (1) in acetone solution with a high apparent association constant, 1.4 x 10(4) M-1. A stoichiometry of 1:1 was also observed by mass spectrometry in the gaseous state. However, in the solid state, as determined by X-ray crystallography, the two complexes of 3a and the previously reported homologous cryptand, bis(1,3,5-phenylene)tri(1,4,7,10,13-pentaoxatridecyl) (3b), with paraquat (1) have 2:1 stoichiometry. A unique feature of these trimolecular pseuclorotaxane-like complexes is that the guest occupies parts of the cavities of two cryptand molecules. For the first time it was found that in cryptand-based complexes, different stoichiometries are possible for the same host-guest pair.
引用
收藏
页码:9367 / 9371
页数:5
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