[38]Octaphyrin(1.1.1.1.1.1.1.1) bearing four methyl moieties at the inner nitrogen sites has been synthesized. This expanded porphyrin has helical chirality as correlated with the orientations of the inner N-methyl groups, exhibiting chiroptical properties as observed in CD Cotton effects from the enantiomers through optical resolution. The chirality of the octaphyrin was retained at r.t. but the racemization occurred at higher temperature as examined by CD spectral changes. The dynamic conversion processes between the enantiomers were investigated by theoretical studies, suggesting the plausible pathways via the intermediates with appropriate conformations.