Structure–Function Relationships of High-Electron Mobility Naphthalene Diimide Copolymers Prepared Via Direct Arylation
| Autor: | Alessandro Luzio, Lars Thomsen, Michael Sommer, Mario Barbatti, Scott E. Watkins, Fritz Nübling, Daniele Fazzi, Rukiya Matsidik, Mario Caironi, Alexander T. Straub, Walter Thiel, Hartmut Komber, Christopher R. McNeill, Ester Giussani, Eliot Gann |
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| Rok vydání: | 2014 |
| Předmět: |
General Chemical Engineering
Heteroatom 02 engineering and technology General Chemistry Dihedral angle Conjugated system 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences chemistry.chemical_compound chemistry Furan Polymer chemistry Materials Chemistry Thiophene Copolymer Density functional theory 0210 nano-technology Selectivity |
| Zdroj: | Chemistry of Materials. 26:6233-6240 |
| ISSN: | 1520-5002 0897-4756 |
| Popis: | 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 α-C–H selectivity is feasible in the DA of π-extended monomers having unsubstituted thiophene or furan units, leading to fully linear materials. Two new naphthalene diimide-based conjugated copolymers—P(FuNDIFuF4) and P(ThNDIThF4), composed of naphthalene diimide (NDI), furan (Fu) or thiophene (Th), and tetrafluorobenzene (F4)—are synthesized. Insight into structure–function 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 π–π-stacking distance in the solid state. P(FuNDI... |
| Databáze: | OpenAIRE |
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