Naphthalene Bis(4,8-diamino-1,5-dicarboxyl)amide Building Block for Semiconducting Polymers
| Autor: | Eric F. Manley, Aidan R. Mouat, Simone Fabiano, Antonio Facchetti, Brian J. Eckstein, Tobin J. Marks, Lin X. Chen, Ferdinand S. Melkonyan |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
business.industry 02 engineering and technology General Chemistry Polymer 010402 general chemistry 021001 nanoscience & nanotechnology Electrochemistry 01 natural sciences Biochemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Colloid and Surface Chemistry Semiconductor chemistry Amide Intramolecular force Polymer chemistry Copolymer Molecule 0210 nano-technology business Naphthalene |
| Zdroj: | Journal of the American Chemical Society. 139:14356-14359 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.7b07750 |
| Popis: | We report a new naphthalene bis(4,8-diamino-1,5-dicarboxyl)amide (NBA) building block for polymeric semiconductors. Computational modeling suggests that regio-connectivity at the 2,6- or 3,7-NBA positions strongly modulates polymer backbone torsion and, therefore, intramolecular π-conjugation and aggregation. Optical, electrochemical, and X-ray diffraction characterization of 3,7- and 2,6-dithienyl-substituted NBA molecules and corresponding isomeric NBA-bithiophene copolymers P1 and P2, respectively, reveals the key role of regio-connectivity. Charge transport measurements demonstrate that while the twisted 3,7-NDA-based P1 is a poor semiconductor, the planar 2,6-functionalized NBA polymers (P2–P4) exhibit ambipolarity, with μe and μh of up to 0.39 and 0.32 cm2/(V·s), respectively. |
| Databáze: | OpenAIRE |
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