Herein two kinds of pillar [5] As one of the main driving forces of the development of supramolecular chemistry, the occurrence of every macrocyclic host molecule has attracted much attention because of their fascinating properties applied in different areas.[1] Pillararenes, [2] as a new type of host molecules since 2008, have drawn more and more attention in recent years. Their syntheses, [3] characterizations [4] and hostÀguest complexations [5] in different medium have been investigated in detail. Functionalizations of pillararenes are very important in order to investigate their properties and applications. A variety of methods have been successfully developed to functionalize pillararenes, [6] one of that is reduction after oxidation which was developed by Huang et al in 2012. [7] In this process, chemists mainly focus their attention on the reduction product, the functionalized pillararenes including hydroquinones, while as an important intermediate, the pillarquinone containing different numbers of benzoquinone units have somewhat been ignored. Furthermore, their hostÀguest complexations have been seldom reported in literature.[