Three thiosemicarbazone-based ligands and corresponding Fe(III) and Co(III) coordination complexes have been synthesised and fully characterised. Crystallographic analysis of all ligands and complexes revealed interesting hydrogen bonding and π-stacking packing arrangements. Magnetic susceptibility and EPR measurements indicate that the Fe(III) complexes are in the low spin state from 4 -300 K. The complexes exhibit significant solution stability (based on UV/vis and NMR data) and the potential for further functionalisation. Such stability gives solution processability and is ideal for the development of advanced supramolecular materials.