Imide‐Functionalized Fluorenone and Its Cyanated Derivative Based n‐Type Polymers: Synthesis, Structure–Property Correlations, and Thin‐Film Transistor Performance. Issue 32 (28th June 2022)

• Record Type: Journal Article
• Authors: Chen, Zhicai; Li, Jianfeng; Wang, Junwei; Yang, Kun; Zhang, Jianqi; Wang, Yimei; Feng, Kui; Li, Bolin; Wei, Zhixiang; Guo, Xugang
• Is Part Of: Angewandte Chemie international edition. Volume 61:Issue 32(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-06-28
• Subjects: Electron-Deficient Building Blocks -- Fluorenone Derivatives -- Imide-Functionalized Polymers -- Organic Thin-Film Transistors -- n-Type Polymers; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202205315
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: The development of high‐performance n‐type polymer semiconductors is powered by the design and synthesis of electron‐deficient building blocks with optimized physicochemical properties. By meticulously installing an imide group onto fluorene and its cyanated derivative, we report here two very electron‐deficient building blocks, imide‐functionalized fluorenone (FOI ) and its cyanated derivative (FCNI ), both featuring a deep‐lying lowest unoccupied molecular orbital energy level down to −4.05 eV and highly coplanar framework, endowing them ideal units for constructing n‐type polymers. Thus, a series of polymers are built from them, exhibiting unipolar n‐type transport character with a highest electron mobility of 0.11 cm 2 V −1 s −1 . Hence, FOI and FCNI offer a remarkable platform for accessing high‐performance n‐type polymers and the imide functionalization of appropriate (hetero)arenes is a powerful strategy for developing polymers with deep‐lying LUMOs for n‐type organic electronics. Abstract : Imide‐functionalization of fluorenone and its cyanated derivative afforded new acceptors FOI and FCNI, respectively, featuring excellent solubility, high planarity, and low‐lying LUMO, which enabled the resulting polymers with unique n‐type transport character in organic thin‐film transistors. The design strategy and synthetic routes to FOI and FCNI are highly informative for the further development of electron‐deficient building blocks for n‐type organic semiconductors.