Diiminoisoindoline (DII) continues to be a useful reagent for the synthesis of phthalocyanine-inspired macrocycles and chelate systems. When combined with pyrazole, indazole, and benzimidazole-based heterocycles, DII forms a chelate that can undergo a template reaction at metal sites to produce phthalocyanine analog compounds. These analogs are ring open macrocycles, where the ring either closes via a non-covalent interaction (biliazine and subbiliazine) or forms a helical structure, the new heliphyrin chelates. This talk will present recent developments and the electrochemical properties of these new phthalocyanine analogs, as well as introduce new isoindoline and phthalazine-based bidentate chelates.