Chemistry Letters, Vol.40, No.7, 739-741, 2011
Synthesis, Physical Properties, and Crystal Structure of Acetetracenylene-1,2-dione
Acetetracenylene-1,2-dione was synthesized by double Friedel-Crafts acylation of tetracene with oxalyl chloride in 46-54% yield. Photophysical, electrochemical, and thermal analysis of the compound revealed its band gap (E-g = 1.77 eV for the solid state), electron-accepting nature (E-pc(red) = 1.35 V vs. Fc/Fc(+)), and thermal stability (T-deomp > 300 degrees C). Single crystals were successfully grown by physical vapor transport, and parallel pi-stacking of the molecules was observed by X-ray crystallography.