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

Von Wiley-VCH zur Verfügung gestellt

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 p-conjugated systems. Although double fused pentagons represented by diketopyrrolopyrrole (DPP) have been utilized as an effective electron-accepting unit, the relatively high-lying frontier molecular orbital levels (FMOs) leave room for further improvement. We report herein on the synthesis of a fluorinated dihydropentalene-1,4-dione (FPD) derivative as a strong electron-accepting unit and prepared D-A-D p-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 compared to those of 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.

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