Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

Abstract

We report novel pseudorotaxanes based on the complexation between pillar[4]arene[1]quinone and 1,10-dibromodecane. The complexation is found to have a 1:1 host–guest complexation stoichiometry in chloroform but a 2:1 host–guest complexation stoichiometry in the solid state. From single crystal X-ray diffraction, the linear guest molecules thread into cyclic pillar[4]arene[1]quinone host molecules in the solid state, stabilized by CH∙∙∙π interactions and hydrogen bonds. The bromine atoms at the periphery of the guest molecule provide convenience for the further capping of the pseudorotaxanes to construct rotaxanes.

Keywords

• host–guest chemistry
• pillar[4]arene[1]quinones
• pillararenes
• pseudorotaxanes
• supramolecular chemistry