Tetracene Dicarboxylic Imide and Its Disulfide: Synthesis of Ambipolar Organic Semiconductors for Organic Photovoltaic Cells

Abstract 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.