The NHC ligand, iCzmi, was prepared in a four-step synthesis (Scheme 1) involving a copper-catalyzed cross-coupling of imidazole to a halogenated aryl group. This was followed by nucleophilic aromatic substitution by carbazole, followed by a palladium-catalyzed ring closing to form the indolo-[3,2,1-jk]carbazole moiety. Finally, N-methylation with iodomethane afforded the NHC ligand as an iodide salt. The Ir(III) complexes were prepared by reaction of the Ir(III) chloro-bridged dimer, the ligand precursor, and a silver salt (Section 2.3). Initially, the silver salt and ligand precursor form a silver-NHC intermediate in-situ, which then reacts with the Ir(III) dimer, affording the final complex. Additionally, the presence of silver salts promote cleavage of the Ir-Cl bond through the formation of AgCl. The isolated yields of both complexes were low, (9 and 14% of Ir(dFppy)2(pmi) and Ir(dFppy)2(iCzmi)), despite full conversion of the dimer to product in each case (ascertained by F NMR spectroscopy analysis). This is attributed to the formation of two isomers in which the NHC ligand is coordinated C^C' or C'^C to the Ir(III) center in each case, which are difficult to separate by column chromatography.