A method for the synthesis of interlocked π-conjugated macrocycles is described. Starting from 2,9-bis(oligothienyl)[1,10]phenanthrolines, (trimethylsilyl)acetylene groups were introduced at the terminal thiophene rings by selective iodination and subsequent Sonogashira–Hagihara coupling. Subsequently, we applied our recently developed metal-template approach to macrocyclization reactions by treating the deprotected acetylenes with cis-[Pt(dppp)Cl2] to yield a platina-macrocycle. Based on this synthetic knowledge, by a multiple transition-metal-template protocol we accomplished the synthesis of a copper(I)–catenate consisting of two interlocked π-conjugated macrocycles which contain oligothiophene, diacetylene and phenanthroline units. Conclusive evidence for the new structures came from a detailed characterization of the platina-macrocycles and catenates by ESI-FT-ICR and tandem mass spectrometry experiments.