I herein report the comprehensive study of a novel class of reduced bis(aryl)acenaphthenequinonediimines (ergo bis(aryl)aminodihydroacenaphthenes) as ligands for catalytic applications. A new synthetic approach towards bis(aryl)acenaphthenequinonediimines and a method for the transformation of the imine to the corresponding amine was developed. The described methods represent a quicker way to obtain the pertinent substances and have a higher scope than traditional syntheses. The elaborated reaction strategy might also serve as a versatile protocol for the preparation of other rigid 1,2- diamine ligands from diketones. The reaction conditions applied in the reduction of the diimines resulted in a significantly increased yield and were applied to the vast majority of the synthesized bis(aryl)acenaphthenequinonediimines. Some of the novel diamines were crystallized and structurally characterized through X-ray diffraction studies. Unfortunately, the attempted total hydrogenation of not only the imine, but also the aromatic functionalities employing catalytic strategies did not succeed in the desired alkylamine scaffold. Despite the fact that the copper mediated oxidation of alcohols to aldehydes showed only little activity when using the diamines as ligands, it nevertheless serves as an example that the reduced bis(aryl)acenaphthenequinonediimines function as ligands, with their catalytic application being subject to future investigations, however. The bis(aryl)acenaphthenequinonediimines prepared by the described method have been employed as ligands for manganese(I) complexes. The spectroscopic properties of these complexes are herein discussed, along with a thorough analytical characterization.