Tuning the circularly polarized luminescence (CPL) is a paramount yet challenging issue in the research field of chiral materials. Here, the chiral supramolecules were constructed with a chiral inducer LL-diphenylalanine (LPFF) and a triphenyl-1,3,5-triazine-derived achiral molecule (DMAC-TRZ) to generate differentiated aggregates, giving rise to tunable responses of CPL. Specifically, the well-defined supercrystallines had an exceptional superior CPL emission located at 485 nm with a large luminescence dissymmetry factor (glum) value as high as +0.16, whereas the formed organic gel possessed a relatively strong CPL emission peaked at 495 nm with a glum value of -0.04 in respect to the water fraction about 50%. The distinguished glum value was assigned to the choice of spatial arrangement of the π-chromophores of DMAC-TRZ responding to the volume water fraction in the H2O/DMSO system, resulting in a tunable glum value. This strategy provides an efficient way to regulate CPL signals by modulating the π-stacking way of organic materials responding to external stimuli.