Novel poly(quinone diimines) from anthraquinones symmetrically disubstituted with solubilizing ethyleneoxy or long chain alkoxy groups have been synthesized and characterized. The disubstituted anthraquinones 1,5-bis(2-methoxyethoxy)anthraquinone (EO(1)AQ), 1,5-bis(2-(2-methoxyethoxy)ethoxy)anthraquinone (EO(2)AQ), 1,5-bis(2-(2-(2-methoxyethoxy)ethoxy)anthraquinone (EO(2)AQ, 1,5-bis(2-(2-2-methoxyethoxy)ethoxy)ethoxy)anthraquinone (EO(3)AQ), 1,5-bis(octyloxy)anthraquinone (15OOAQ), 2,6-bis(octyloxy)anthraquinone (26OOAQ), and 1,4-bis(octyloxy)anthraquinone (14OOAQ) were synthesized and condensed with aniline in the presence of titanium tetrachloride and 1,4-diazabicyclo[2.2.2]octane to give N,N’-diphenyl-1,5-bis(2-methoxyethoxy)(n)anthraquinone 9,10-diimine (DEO(n)AQ, n = 1-3), N,N-diphenyl-1,5-bis(octyloxy)anthraquinone 9,10-diimine (15DOOAQ), and N,N’-diphenyl-2,6-bis(octyloxy)anthraquinone 9,10-diimine (26DOOAQ), respectively, as model compounds for the polymers. The relative stereochemistry of these diimines was determined by H-1 NMR spectroscopy. Polycondensation of the disubstituted anthraquinones with 4,4’-thiodianiline (SDA) gave high molecular weight (M(w) 30 000) poly(anthraquinone diimines) and large macrocycles. Polycondensation of 1,4-phenylenediamine (PDA) with EO(2)AQ gave high molecular weight (M(w) 14 000) polyaromatic anthraquinone diimines. PDA gave molecular weights of M(w) 5000-23 000 for the bis(octyloxy)-substituted anthraquinones. The molecular weights of polymerizations incorporating PDA are lowered due to steric interactions of successive repeat units and solubility constraints.