A New Cryptand/Paraquat [2]Pseudorotaxane

Shijun Li; Feihe Huang; Lev N. Zakharov; Carla Slebodnick; Arnold L. Rheingold; Harry W. Gibson

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A New Cryptand/Paraquat [2]Pseudorotaxane

Shijun Li 1 #,Feihe Huang 1 *,Lev N. Zakharov 2,Carla Slebodnick 3,Arnold L. Rheingold 2,Harry W. Gibson 3

1.Department of Chemistry, Zhejiang University

2.Department of Chemistry and Biochemistry, University of California

3.Department of Chemistry, Virginia Polytechnic Institute and State University

*Correspondence author

#Submitted by

Subject:

Funding: 教育部博士点基金,the National Science Foundation of USA（No.20070335152,DMR0097126）

Opened online:20 July 2009

Accepted by: none

Citation: Shijun Li,Feihe Huang,Lev N. Zakharov.A New Cryptand/Paraquat [2]Pseudorotaxane[OL]. [20 July 2009] http://en.paper.edu.cn/en_releasepaper/content/33935

A new cryptand/paraquat [2]pseudorotaxane and its crown ether analog were synthesized and charac-terized by proton NMR, mass spectrometry, and single crystal X-ray analysis. The Job plots based on proton NMR data demonstrated that both the complex between cryptand 1 and paraquat derivative 2a and the complex between bis(p-phenylene)-34-crown-10 (3) and paraquat derivative 2b have 1:1 stoichiometry in solution. The apparent association constants (Ka,exp) of 1•2a and 3•2b calculated for 1:1 complexes were 1.4 ( 0.2)  104 and 4.7 ( 0.5)  102 M1, respectively. X-ray analysis showed that 1•2a is stabilized by ten hydrogen bonds and face-to-face -stacking interactions in the solid state, while 3•2b is stabilized by four hydrogen bonds and face-to-face -stacking interactions. As well as in the X-ray structure of 1•2c, a water molecule acts as a hydrogen bridge between the -protons of 2a and the ether oxygen atoms of 1 in 1•2a. The successful preparation of 1•2a demonstrated that the tert-butyl group is not big enough to be a stopper for rotaxanes based on 1.

Keywords:host-guest system;self-assembly;pseudorotaxane, cryptand;paraquat

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