Fluorinated Dihydropentalene-1,4-Dione: A Strong Electron-Accepting Unit with Organic Semiconductor Characteristics
Fluorinated Dihydropentalene-1,4-Dione: A Strong Electron-Accepting Unit with Organic Semiconductor Characteristics
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氟化二氢戊二烯-1,4-二酮：具有有机半导体特性的强电子接受单元
DOI：
10.1002/chem.202203873
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发表时间：
2023
期刊：
影响因子：
--
通讯作者：
Y. Ie
中科院分区：
文献类型：
--
作者：
S. Yokoyama;Y. Ie
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.
