Complementary double hydrogen-bonded CT complexes of TTF having uracil moiety

Abstract We designed and prepared a TTF derivative with N 1 - n -butyl-substituted uracil (T n bU) which has the complementary double hydrogen-bonding (HB) sites and high solubility toward common organic solvents. The cyclic voltammogram of T n bU in DMF exhibited two-stage one-electron reversible oxidation behavior ( E 1 =−0.102 V ; E 2 =+0.095 V versus Fc/Fc + ), indicating slightly higher donating ability compared with TTF itself. The crystal structure of T n bU consists of the π-stacking dimer between TTF moieties and complementary double HB dimer between uracil moieties. The CT complex of T n bU with cyananilic acid (H 2 CNAL) exhibited alternated stacking type structure and complementary double HB between uracil moiety of T n bU and monoanion of H 2 CNAL, hydrogen cyananilate (HCNAL).