Based on the concept of dual-directionality, the synthesis of two novel zinc(II)-containing phthalocyanine (Pc-ene1) and azaphthalocyanine (AzaPc-ene1) macrocycles bearing dual directional (up/down) allyl moieties on their rims is reported. Their structural identification, that is, NMR, FT-IR, UV-vis, MALDI-TOF spectral data, single crystal X-ray diffraction, and CHN elemental analyses, along with their nonaggregating behaviors in solvated media and crystalline forms has been confirmed.