STRUCTURAL AND ELECTROCHEMICAL PROPERTIES OF A NOVEL N,N'-DIALKYL-SUBSTITUTED QUINONE DIIMINE

0,11,11a,14,14a-tetradecahydroquino[2,3-b]acridine 5, formed by a Lewi s acid-catalyzed biscyclization of N-arylbisimine 3 and subsequent aut oxidation, represents the first stable example of the unexplored class of N,N'-dialkyl-substituted quinone diimines. The X-ray crystal struc ture of 5 exhibits the following features: space group P2(1)/c; a ribb on-like arrangement Of two parallel strands along the b-axis. The smal lest intermolecular distance between two quinoid systems is 4.846 Angs trom and therefore any close aromatic contacts in this material can be precluded. A chemically reversible single electron reduction at E-0 = -1.87 V has been observed by cyclic voltammetry.