Single-walled carbon nanotubes (SWNTs) with positive (P-) and minus (M-) handed helicity according to wrapping orientation of graphene exhibits the identical optical property for their isomer. The symmetry breaking of SWNT is expected to alter their properties that are essential for fundamental study and applications, and, however needs to be understood thoroughly. In this presentation, we report the photoluminescence (PL) and binding affinity (K_a) differentiation of SWNT isomers with varying concentration of flavin mononucleotide (FMN) as chiral surfactant. While the FMN concentration was increasing, a position-shifted second PL revealed near initial PL, and the shifted direction from the initial PL depends on the modality of SWNT. Using optical titration method which used achiral surfactant as a titrant, PL trajectories of P- and M-SWNTs display universal two-step inflection upon replacement with FMN whose intensity corresponds to the abundance of SWNTs isomers which is confirmed by the circular dichroism measurement. The enantiomeric excess (ee) of SWNT ensemble was calculated based on the PL intensity difference, and the ee value decrease to less than 20% with increasing FMN concentration. Via FMN-based density gradient ultracentrifugation (DGU) distinct, PL shift trend according to SWNT handedness was observed at different density of DGU medium. This phenomenon is suggested to derive from the unidirectional torsion caused by the P-type FMN helix on the isomeric SWNT surface, and the resulting optical transition shift exhibits opposite shift trends depending on handedness and modality. Finally, we determined ee of SWNT dispersed by sodium cholate, universally used surfactant, using FMN as a titrant, and confirmed the scalability of this general scheme.