A noncovalently assembled porphyrinic catenane consisting of two interlocking [43]-membered rings

摘要

A new macrocycle and the corresponding [2]catenane were prepared quantitatively from relatively large organic fragments using coordination chemistry bonds only (Zn-N bonds for the ring and Cu-N bonds for the catenane). The two constitutive macrorings of the [2]catenane are 43-membered rings. The organic components consist of a bis-Zn porphyrin and a 1,10-phenanthroline derivative, both fragments being significantly larger than those previously used for making related compounds. The catenane was assembled in two steps from a bis-Zn porphyrin and a 2,9-di(4"-pyridyl-4'-phenyl)-1,10-phenanthroline. In a first step the entwined copper(I) complex of the phenanthroline derivative was formed via Cu(I)-N interactions. Subsequently, a double ring closing reaction was performed by coordination of two equivalents of bis-Zn porphyrin to the entwined copper(I) complex. The tetraporphyrinic [2]catenane was thus obtained thanks to the formation of four Zn(n)-pyridine bonds. It has a high association constant, 4 x 10~(10) M~(-2), due to the good geometrical fit between the constituents.