Recently, π-π stacked antiaromatic π-systems have received considerable attention because theycan exhibit stacked-ring aromaticitydue tosubstantial intermolecular orbital interactions. Here, we report three antiaromatic norcorrole dimers that self-assemble to form supramolecular architectures through chiral self-sorting. A2,2'-linked norcorrole dimerwith 3,5-di-tert-butylphenyl groups forms aπ-stacked dimer both in solid and solution statesvia homochiral self-sorting. Its association constant in solution is(3.6 ± 1.7) × 105M-1at 20 °C. In the solid state,3,3'-linked norcorrole dimerswith 3,5-di-tert-butylphenyl and phenyl groups afford macrocyclic and helical supramolecular assemblies via heterochiral and homochiral self-sorting, respectively. Notably, the subtle modification in the substituent resulted in a complete change in the structure of the aggregates and the chiral self-sorting mode. The present findings demonstrate that structural manipulation in antiaromatic monomer units leads to the formation of various supramolecular assemblies on the basis of the attractive interactions between antiaromaticπ-systems.