O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes
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| Názov: | O-Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed-Valence Complexes |
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| Autori: | Dordevic L., Valentini C., Demitri N., Meziere C., Allain M., Salle M., Folli A., Murphy D., Manas-Valero S., Coronado E., Bonifazi D. |
| Prispievatelia: | Dordevic, L., Valentini, C., Demitri, N., Meziere, C., Allain, M., Salle, M., Folli, A., Murphy, D., Manas-Valero, S., Coronado, E., Bonifazi, D. |
| Informácie o vydavateľovi: | Wiley-VCH Verlag |
| Rok vydania: | 2020 |
| Zbierka: | Padua Research Archive (IRIS - Università degli Studi di Padova) |
| Predmety: | electrocrystallization, electron paramagnetic resonance, heteroatom doping, molecular graphene, polycyclic aromatic hydrocarbons |
| Popis: | Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities. |
| Druh dokumentu: | article in journal/newspaper |
| Jazyk: | English |
| Relation: | info:eu-repo/semantics/altIdentifier/wos/WOS:000508993100001; volume:59; issue:10; firstpage:4106; lastpage:4114; numberofpages:9; journal:ANGEWANDTE CHEMIE. INTERNATIONAL EDITION; https://hdl.handle.net/11577/3470657 |
| DOI: | 10.1002/anie.201914025 |
| Dostupnosť: | https://hdl.handle.net/11577/3470657 https://doi.org/10.1002/anie.201914025 |
| Rights: | info:eu-repo/semantics/openAccess |
| Prístupové číslo: | edsbas.CD3C3AED |
| Databáza: | BASE |
Nájsť tento článok vo Web of Science | Abstrakt: | Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the π-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixed-valence (MV) complexes were grown in which the organic salts organize into face-to-face π-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar π-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that π-extension of heteroatom-doped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities. |
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| DOI: | 10.1002/anie.201914025 |