Expanded porphyrins represent emerging structures in realizing topological chirality; however, their inherent flexibility has hampered the effective chiral resolution. Herein, we rationally designed a decaphyrin 9, which could be separated into its enantiomers in the free-base form. The enantiomers showed noteworthy chiroptical properties, e.g., the intense circular dichroism response in the visible spectrum, and high absorption dissymmetry factors (gabs) of 0.036 at 618 nm. Theoretical analyses further explained the origin of the high gabs value.