Tetracene dicarboxylic imide and its disulfide: synthesis of ambipolar organic semiconductors for organic photovoltaic cells.
We have designed and synthesized a new donor/acceptor-type tetracene derivative by the introduction of dicarboxylic imide and disulfide groups as electron-withdrawing and -donating units, respectively. The prepared compounds, tetracene dicarboxylic imide (TI) and its disulfide (TIDS) have high chemical and electrochemical stability as well as long-wavelength absorptions of up to 886 nm in the thin films. The crystal packing structure of TIDS molecules features face-to-face π-stacking, derived from dipole-dipole interactions. Notably, TIDS exhibited ambipolar properties of both electron-donating and -accepting natures in p-n and p-i-n heterojunction organic thin-film photovoltaic devices. Accordingly, TI and TIDS are expected to be promising compounds for designing new organic semiconductors.
Department of Chemistry, The University of Tokyo, Bunkyo-ku, Tokyo, Japan. tokamo@sanken.osaka-u.ac.jp
Toshihiro
T
Okamoto
Tsuyoshi
T
Suzuki
Hideyuki
H
Tanaka
Daisuke
D
Hashizume
Yutaka
Y
Matsuo
D004220:Disulfides / Q000138:chemical synthesis / Q000737:chemistry*; D011211:Electric Power Supplies; D004563:Electrochemistry; D007094:Imides / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D012666:Semiconductors
D004220:Disulfides; D007094:Imides