Synthesis of Perylene Imide Diones as Platforms for the Development of Pyrazine Based Organic Semiconductors
| Autor: | J. Teodomiro López Navarrete, Rocío Ponce Ortiz, Paula de Echegaray, Guzmán López-Espejo, Carlos Seoane, José L. Segura, Iratxe Arrechea-Marcos, Rafael Juárez, María M. Ramos, María J. Mancheño |
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| Rok vydání: | 2016 |
| Předmět: |
Pyrazine
Organic Chemistry 02 engineering and technology Nuclear magnetic resonance spectroscopy 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry 01 natural sciences 0104 chemical sciences Organic semiconductor chemistry.chemical_compound Terthiophene chemistry Thiophene 0210 nano-technology Imide Two-dimensional nuclear magnetic resonance spectroscopy Perylene |
| Zdroj: | The Journal of Organic Chemistry. 81:11256-11267 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.6b02214 |
| Popis: | There is a great interest in peryleneimide (PI)-containing compounds given their unique combination of good electron accepting ability, high abosorption in the visible region, and outstanding chemical, thermal, and photochemical stabilities. Thus, herein we report the synthesis of perylene imide derivatives endowed with a 1,2-diketone functionality (PIDs) as efficient intermediates to easily access peryleneimide (PI)-containing organic semiconductors with enhanced absorption cross-section for the design of tunable semiconductor organic materials. Three processable organic molecular semiconductors containing thiophene and terthiophene moieties, PITa, PITb, and PITT, have been prepared from the novel PIDs. The tendency of these semiconductors for molecular aggregation have been investigated by NMR spectroscopy and supported by quantum chemical calculations. 2D NMR experiments and theoretical calculations point to an antiparallel π-stacking interaction as the most stable conformation in the aggregates. Investigation of the optical and electrochemical properties of the materials is also reported and analyzed in combination with DFT calculations. Although the derivatives presented here show modest electron mobilities of ∼10 |
| Databáze: | OpenAIRE |
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