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

We designed and prepared a TTF derivative with N1-n-butyl-substituted uracil (TnbU) which has the complementary double hydrogen-bonding (HB) sites and high solubility toward common organic solvents. The cyclic voltammogram of TnbU in DMF exhibited two-stage one-electron reversible oxidation behavior (E1=−0.102 V; E2=+0.095 V versus Fc/Fc+), indicating slightly higher donating ability compared with TTF itself. The crystal structure of TnbU consists of the π-stacking dimer between TTF moieties and complementary double HB dimer between uracil moieties. The CT complex of TnbU with cyananilic acid (H2CNAL) exhibited alternated stacking type structure and complementary double HB between uracil moiety of TnbU and monoanion of H2CNAL, hydrogen cyananilate (HCNAL).