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Dipyrrolyldiketones are essential building units of anion-responsive π-electronic molecules and ion-pairing assemblies. Here, we demonstrated that they form complexes with Cu II characterized by planar geometries. The solid-state stacking assembled structures, as revealed by single-crystal X-ray analysis, were modulated by the substitution of pyrrole units. The rectangular shapes of the Cu II complexes resulted in the formation of mesophases upon introduction of aliphatic chains.