The synthesis and spectroscopic properties of macrocyclic polyethers containing two different aromatic moieties and their [2] catenanes incorporating cyclobis(paraquat-p-phenylene)

The absorption spectra and luminescence properties of six new [2]catenanes are reported. The new catenanes are formed as a result of a template reaction of cyclobis(paraquat-p-phenylene) with six new derivatives of bis-p-phenylene-34-crown-10 in which the p-phenylene rings have been replaced variously by p-xylyl units, 1,5-, 1,6-, 2,6-, and 2,7-naphtho units, and a naphthalene-2,6-dimethylyl ring system. Dynamic 1H NMR spectroscopy reveals that some of the [2]catenanes exhibit translational isomerism (right). Comparison with the properties of simple model compounds shows the presence of intra- and intermolecular electronic interactions between the component units of the crown ethers and the catenanes.