An interdigitated functionally rigid [2]rotaxane

Abstract

The synthesis of a functionally rigid [2]rotaxane incorporating pi-electron rich 1,5-disubstituted naphthalene (NP) ring systems, encircled by the pi-electron deficient tetracationic cyclophane, cyclobis(paraquat-p-phenylene), is described; in the solid state, the molecules of this donor-acceptor [2]rotaxane line themselves up in parallel pi-pi stacks of alternating NP ring systems and bipyridinium units, a affording an interdigitated superstructure.