A series of novel chiral platinum complexes 1–8 (R = 4-NEt2 (1), 4-F (2), 5-CF3 (3), 5-Cl (4), 5-OCF3 (5), 4-CF3 (6), 5-F (7), 5-MeO (8)) was prepared and their circularly polarized luminescence (CPL) properties were compared with those of the non-substituted analogue 9 (R = H). The complexes showed multi-color (green, yellow, and red) phosphorescence in the solution state, depending on the substitution position of the functional group of the ligands. The chiral complexes exhibited CPL with absolute luminescence dissymmetry factor (glum) of up to the 1.3 × 10−3 in the dilute solution state. Acid-induced CPL was also achieved by the protonation of the diethylamino group of complex 1 with CH3SO3H. Density functional theory (DFT) calculations were conducted to further understand the structure dependence of the chromogenic behavior of these complexes.