Two enantiomeric gelator molecules containing anthracene moiety were assembled at the air/water interface and several new insights into the films of the gelator molecules were revealed. When these molecules were spread at the air/water interface, they formed the nanorod structured monolayers and could be subsequently transferred to the solid substrate. The formed Langmuir-Blodgett (LB) films showed both optical activity and circularly polarized luminescence (CPL) due to the chirality transfer upon assembling. The dissymmetric factors of the CPL in the LB films were enhanced nearly 5 times than those in gel systems. Through the formation of the organized nanofilms, the arrangement of the molecules become compact and the film showed enantioselectivity to chiral species, whereas the molecular solution could not.