Abstract: Cu (1) catenates and the corresponding metal-free catenands in which one or both constitutive rings are oriented have been synthesized and characterized. Ring orientation is achieved by an appropriate substitution on the phenanthroline core of the macrocycle. Cu (1) catenates which contain two oriented rings are topologically chiral. Their chirality has been observed by'H-NMR spectroscopy in an optically active medium. Indeed, a splitting ...