The targeted complexes required the synthesis of eight trimethylsilylated 2phenylpyridine ligands. Of these, three had already been reported in the literature: (2-phenyl-5-trimethylsilylpyridine (N5Sippy), 2-(3-trimethylsilylphenyl)-5-trimethylsilylpyridine (C3N5Si2ppy) and 2-(4-trimethylsilylphenyl)-5-trimethylsilylpyridine (C4N5Si2ppy)), while the remaining five ligands are new. The ligands were synthesised through the Suzuki-Miyaura coupling of appropriately substituted phenyl boronic acids and 2bromopyridine (Figure ). Trimethylsilyl-substituted phenyl boronic acids are commercially available, while trimethylsilyl-substituted 2-bromopyridine starting materials were readily obtained from dibromopyridine precursors. Isolated yields of the ligands were poor to moderate, ranging from 15% to 66%, the low yields were due to the volatile nature of the compounds resulting in product loss during removal of solvents under reduced pressure. The target complexes were synthesised using a two-step reaction protocol. Firstly, the ligands were reacted with [Ir(COD)Cl]2 to form a chloro-bridged iridium dimer, which was then reacted with picolinic acid in the presence of an inorganic base to afford the target complexes (Figures and). Most of the complexes were isolated in good to excellent yields (dimers formed in > 80% yield, picolinate complexes in > 60% yield). The lower isolated yields for some highly silylated complexes was attributed to their higher solubility, which adversely affected the recovery of material during recrystallisation.