JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, v.128, no.51, pp.16514 - 16515
Abstract
A new N-heterocyclic carbene architecture comprising a 1,4-naphthoquinone annulated to 1,3-dimesitylimidazolylidene (NpQ−NHC) was synthesized in two high yielding steps from commercially available starting materials. The free NpQ−NHC was characterized (solution and solid-state) and was used to synthesize various Rh and Ag complexes that ranged in π-electron density. Enabled by the quinone moiety, the π-systems of these complexes were analyzed using infrared spectroscopy and cyclic voltammetry. In contrast to previous reports, π-backbonding was found to be non-negligible and was directly influenced by the metal's electronic character.