Novel alkyl- and aryl-bridged dithioether-diketones were prepared via an N,N,N-triethyl-N-(propan-2-onyl)ammonium ion and several dithiols. These dithioether-diketones were then used as templates to make derivatives with other N, O, and S donor groups. Some ortho-functionalized anilines formed polydentate metal-chelaters with N₂O₂S₂-donor sets. Structural, spectroscopic, and electrochemical data for these ligands and complexes will be presented.