Enantiopure, luminescent, cyclometalated Ir(III) complexes with N-heterocyclic carbene-naphthalimide chromophore: design, vibrational circular dichroism and TD-DFT calculations

A series of chiral cyclometalated iridium complexes of the type [Ir(C boolean AND N)(2)(C boolean AND C:)], {(C boolean AND N) = ppy (2); dfppy (3)} featuring a naphthalimide N-heterocyclic carbene ligand (C boolean AND C:) = (Naphthalimide-NHC) are described and fully characterized. The racemic complexes rac-2 and rac-3 were resolved via chiral column chromatography techniques into their corresponding enantiopure species Delta-2, Lambda-2, Delta-3, Lambda-3 as confirmed by their CD curves. This unique class of molecules containing organic and inorganic chromophores might be used as a platform to probe the stereochemical effect on the photophysical properties. Vibrational circular dichroism (VCD) was used as an important tool to assign successfully the stereochemistry of the enantiomers. TD-DFT calculations are also advanced to support the experimental studies and to rationalize the observed results.