The preparation of the first enantiopure cycloplatinated complexes bearing a bidentate, helicenic N-heterocyclic carbene and a diketonate ancillary ligand is presented, along with their structural and spectroscopic characterization based on both experimental and computational studies. The systems exhibit long-lived circularly polarized phosphorescence in solution and in doped films at room temperature, and also in a frozen glass at 77 K, with dissymmetry factor glum values ≥10-3 in the former and around 10-2 in the latter.