Using electromagnetic modeling and analytical methods, we study the optimal conditions of an enantioselective optical process (EOP) through the interaction potential between enantiomers and localized chiral near-fields created by asymmetric plasmonic crescent moon (PCM) nanoapertures when it is illuminated with circularly polarized light. We introduce a chiral dissymmetry factor which measures the degree of chiral discrimination of the EOP and we found that it depends mainly on the differential field intensification, near-field optical chirality and the handedness of the enantiomers. Our results prove that a sub-10-nm non-magnetic enantiomer pair of chiral spherical molecules with chirality parameter up to $\pm 0.005$±0.005 can be passively separated under dual-symmetric conditions. The method and the proposed nanostructure may enable all-optical enantioseparation of single-chiral macromolecules, such as proteins and carbohydrates.
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