In summary, we successfully synthesized a fully π-conjugated interactions. This enables strong through-space electronic coupling, significantly reducing the diradical and antiaromatic character. Notably, in the solid state, 1-Zn 4+ with SbCl6 -counterions exhibits a unique electronic configuration featuring two annihilated triplet aromatic macrocycles, further stabilizing the system. These findings highlight how π-conjugated molecules with a catenane topology adjust their geometries and electronic configurations to achieve the lowest energy states. Moreover, they provide an experimental platform to explore the interplay of molecular magnetism and conduction in entangled molecules, including Aharonov-Bohm effects. This study advances our understanding of and ability to design novel topological π-conjugated systems with emergent optical, electronic, and magnetic properties, opening avenues for further exploration of their potential applications.