The photophysical properties of the two pairs of chiral molecules are shown in Figure . The emission wavelengths in THF solution are much longer than the solid state as concluded in Table , which can be explained by the restriction of intramolecular vibration (RIV) mechanism . Both pairs of chiral molecules have obvious AIE phenomenon in THF/Water solution (Figure , 1e), with emission intensity greatly increasing when water fraction increases. The fluorescence intensity of meta position molecules showed 46-fold increase in aggregate state compared to pure THF solution state. The typical AIE phenomenon thus shows the advantage for OLED applications and has made huge progress . Also, the emission peak wavelength showed a redshift, and then a blue shift with water fraction increases, which is related to the increased solvent polarity and aggregation of the molecules. The emission of pure THF solutions were measured for four molecules and R/S-P-TBBTCN have near infrared (NIR) emissions at 705 nm and R/S-M-TBBTCN have NIR emission at 770 nm, as shown in Figure and insert. It can be explained that the D-A structure gives a valid way to enhance the electron delocalization effect and achieves a longer emission wavelength. The molecular design includes the modification of the TPA substitution position from pare to meta to enhance the intramolecular steric hindrance. The 20 nm red-shift of meta-substituted molecules compare to the para-substituted ones in THF solution suggests a more twisted structure, stable charge transfer (CT) state, and smaller ΔEST . In the lifetime measurement test, the para-substituted molecules showed a lifetime of 9.0 ns and 9.3 ns for S and R configurations, respectively. As for meta-substituted ones, the lifetime