A family of heteroleptic (C boolean AND N)(2)Ir(acac) and homoleptic fac-Ir(C boolean AND N)(3) complexes have been synthesized and their photophysical properties studied (where C boolean AND N = a substituted 2-phenylpyridine and acac = acetylacetonate). The neutral Delta and Lambda complexes were separated with greater than 95% enantiomeric purity by chiral supercritical fluid chromatography, and the solution circular dichroism and circularly polarized luminescence spectra for each of the enantio-enriched iridium complexes were obtained. The experimentally measured emission dissymmetries (g(em)) for this series compared well with predicted values provided by time-dependent density functional theory calculations. The discovered trend further showed a correlation with the dissymmetries of ionic, enantiopure hemicage compounds of Ru(II) and Zn(II), thus demonstrating the applicability of the model for predicting emission dissymmetry values across a wide range of complexes.