Structure鈥揊unction Relationships of High-Electron Mobility Naphthalene Diimide Copolymers Prepared Via Direct Arylation

详细信息    查看全文

• 作者：Alessandro Luzio ; Daniele Fazzi ; Fritz N眉bling ; Rukiya Matsidik ; Alexander Straub ; Hartmut Komber ; Ester Giussani ; Scott E. Watkins ; Mario Barbatti ; Walter Thiel ; Eliot Gann ; Lars Thomsen ; Christopher R. McNeill ; Mario Caironi ; Michael Sommer
• 刊名：Chemistry of Materials
• 出版年：2014
• 出版时间：November 11, 2014
• 年：2014
• 卷：26
• 期：21
• 页码：6233-6240
• 全文大小：468K
• ISSN：1520-5002

文摘

Direct arylation (DA) is emerging as a highly promising method to construct inexpensive conjugated materials for large-area electronics from simple and environmentally benign building blocks. Here, we show that exclusive 伪-C鈥揌 selectivity is feasible in the DA of 蟺-extended monomers having unsubstituted thiophene or furan units, leading to fully linear materials. Two new naphthalene diimide-based conjugated copolymers鈥擯(FuNDIFuF₄) and P(ThNDIThF₄), composed of naphthalene diimide (NDI), furan (Fu) or thiophene (Th), and tetrafluorobenzene (F₄)鈥攁re synthesized. Insight into structure鈥揻unction relationships is given by density functional theory (DFT) calculations and variety of experimental techniques, whereby the effect of the heteroatom on the optical, structural, and electronic properties is investigated. The use of furan (Fu) allows for enhanced solubilities, a smaller dihedral angle between NDI and Fu as a result of the smaller size of Fu, and a smaller 蟺鈥撓€-stacking distance in the solid state. P(FuNDIFuF₄) also exhibits a more edge-on orientation compared to P(ThNDIThF₄). Despite these advantageous properties of P(FuNDIFuF₄), P(ThNDIThF₄) exhibits the highest electron mobility: 鈭?.3 cm²/(V s), which is a factor of 鈭? greater than that of P(FuNDIFuF₄). The enhanced OFET performance of P(ThNDIThF₄) is explained by reduced orientational disorder and the formation of a terrace-like thin-film morphology.