Isophlorins and its analogues bridge be structural features between porphyrins and annulenes. Invariably they are known to be unstable but can be stabilized by appropriate substituents in the core and periphery of a macrocycle. Solid-state characterization of these 20 pi systems displays planarity for each macrocycle and even in their supramolecular arrangement due to C-H center dot center dot F-C interactions.