Self-Sorting of Four Organic Molecules into a Heterowheel Polypseudorotaxane

The social self-sorting supramolecular assembly is described by non-covalent interactions among four organic components. Toward this goal, a series of self-sorting systems have been investigated by mixing two or three different compounds; naphthyl-bridged bis(-cyclodextrin), N,N-dioctyl-4,4-bipyridinium, 2,6-dihydroxynaphthalene, and cucurbit[8]uril. The influence of alkyl chains of viologen derivatives and the binding abilities of these systems have also been studied. Their integrative self-sorting led to the exclusive formation of the purple supramolecular heterowheel polypseudorotaxane. The heterowheel polypseudorotaxane is a thermodynamically stable self-sorted product, and consists of two different macrocycles with three sorts of different non-covalent interactions. Its structure was established by NMR spectroscopy and UV/Vis absorption spectroscopy, transmission electron microscopy (TEM), atomic force microscopy (AFM), dynamic light-scattering (DLS), diffusion-ordered spectroscopy (DOSY), and viscosity measurements.