Herein, we report the synthesis of a novel carbaporphyrin incorporating perylene diimide (PDI) and dipyrromethane units. The twisted plane of the PDI subunits imbues carbaporphyrin with intriguing conformational chirality and stable chiroptical properties. Both experimental and theoretical studies reveal that the unique properties arise from the rigidly conjugated macrocyclic architecture and the reduced interchromophoric distance. This work successfully integrates PDIs into carbaporphyrins, thereby expanding their structural diversity and functional potential.