Heterocyclic heptacene analogs – 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles as charge transport materials
| Autor: | Povilas Adomėnas, Sigitas Tumkevicius, Saulius Juršėnas, Alytis Gruodis, Karolis Kazlauskas, Vygintas Jankauskas, Tomas Serevičius, Renaldas Rimkus, Regimantas Komskis |
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| Rok vydání: | 2016 |
| Předmět: |
Organic electronics
chemistry.chemical_classification Heptacene Chemistry Process Chemistry and Technology General Chemical Engineering Aryl Heteroatom 02 engineering and technology Conjugated system 010402 general chemistry 021001 nanoscience & nanotechnology Photochemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Organic chemistry Molecule Ionization energy 0210 nano-technology Alkyl |
| Zdroj: | Dyes and Pigments. 124:133-144 |
| ISSN: | 0143-7208 |
| DOI: | 10.1016/j.dyepig.2015.08.029 |
| Popis: | Owing to extended π-electron system higher polyacenes are promising materials for organic electronics, however realization of higher conjugation of acenes results in their instability under ambient conditions. We now report on synthesis, optical and electrical characterization of nitrogen heteroatom containing heptacene analogs – 8H-16,17-epoxydinaphto[2,3-c:2′,3′-g]carbazoles – decorated with various alkyl and aryl side-groups. V-shape geometry, incorporation of nitrogen heteroatom and introduced epoxy bridge ensure higher oxidative stability of the compounds as compared to analogous polyacenes. Additionally, the alteration of the molecular structure with various side-groups, either conjugated or non-conjugated, enabled the tuning of ionization potential from 4.7 eV to 5.5 eV with further gain in compound stability. This ensures of hole drift mobility up to 8 × 10−4 cm2/(V s) at 1 MV/cm for thick wet-casted films under ambient conditions. Peculiarities of forbidden lowest excited states in the V-shaped N-heptacenes are revealed based on detailed optical characterization and density functional modeling. |
| Databáze: | OpenAIRE |
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