M. Pepitone, S. Hardaker, R. V. Gregory
Jan 3, 2003
Citations
0
Influential Citations
29
Citations
Journal
Chemistry of Materials
Abstract
We report the synthesis of novel 3,4-ethylenedioxythiophene (EDOT) derivatives and the investigation of their photoluminescent properties. Lithiation of EDOT followed by the conversion to the 2-substituted zinc chloride or Grignard derivatives (useful for subsequent coupling reactions using organopalladium and organonickel chemistry) led to the formation of 2,5-bis[(3,4-ethylenedioxy)thien-2-yl]-thiazole (1), 2,5-bis[(3,4-ethylenedioxy)thien-2-yl]-3-alkylthiophene (2, 3), and 2,5-bis[(3,4-ethylenedioxy)thien-2-yl]-toluene (4). The lithiated EDOT provided a route for the formylated species followed by a Knoevenagel condensation which led to the cyanovinylene derivatives 1,4-bis[1-cyano-2-{(3,4-(ethylenedioxy)thien-2-yl}vinyl]benzene (5), 1,4-bis[1-cyano-2-{(3,4-(ethylenedioxy)thien-2-yl}vinyl]-2,5-dimethoxybenzene (6). The lithated EDOT also provided a convenient method for preparation of 2,5-bis[(3,4-ethylenedioxy)thien-2-yl]-1,3,4-oxadiazole (12) by the hydrazide method. These materials exhibit blue to r...