Recently, covalently linked or self-assembled porphyrin array systems have attracted much attention for their enhanced two-photon absorption (TPA) behaviors. In this study, we have investigated the TPA properties of various dihedral angle controlled, directly linked porphyrin dimers and arrays to elucidate the relationship between the pi-conjugation pathway and TPA properties. We have demonstrated a strong correlation between pi-conjugation (aromaticity) and TPA properties in porphyrin assemblies.