Maximum confusion in porphyrinoids can be achieved by inter-linking heterocycles only through 2,4-connectivity. 20π confused porphycene and 30π expanded porphycene represent examples with the highest number of confused heterocyclic units in a given macrocycle. They significantly differ from the parent 20π porphycene and 30π hexaphyrin in their structural, electronic and redox properties due to the cross conjugation arising from the 2,4-connectivity of the heterocycle. They have been characterized by single crystal X-ray diffraction studies and their aromatic features have been substantiated by quantum chemical calculations.