Fluorinated Dihydropentalene-1,4-Dione: A Strong Electron-Accepting Unit with Organic Semiconductor Characteristics.

The development of electron-accepting units is of significant importance because the construction of donor (D)-acceptor (A) configurations is an effective strategy for tuning the electronic properties of π-conjugated systems. Although doubly fused pentagons represented by diketopyrrolopyrrole (DPP) have been used as an effective electron-accepting unit, the relatively high-lying frontier molecular orbital levels (FMOs) leave room for further improvement. We report herein the synthesis of a fluorinated dihydropentalene-1,4-dione (FPD) derivative as a strong electron-accepting unit and the development of D-A-D π-extended molecules. X-ray analyses revealed that the presence of fluorine atoms contributed to the formation of high planar structures and slipped-stacked packing. Electrochemical measurements indicated that the FPD derivatives showed relatively lower FMO energy levels than the corresponding DPP-containing derivatives. The D-A-D molecule based on terthiophene and FPD showed semiconducting responses. This study demonstrates that the FPD unit can function as a new acceptor unit for organic semiconductors.