Dehydrative pi-extension to nanographenes with zig-zag edges
Lungerich D, Papaianina O, Feofanov M, Liu J, Devarajulu M, Troyanov S, Maier S, Amsharov K (2018)
Publication Status: Published
Publication Type: Journal article
Publication year: 2018
Journal
Publisher: NATURE PUBLISHING GROUP
Book Volume: 9
Article Number: ARTN 4756
DOI: 10.1038/s41467-018-07095-z
Open Access Link: https://www.nature.com/articles/s41467-018-07095-z
Abstract
Zig-zag nanographenes are promising candidates for the applications in organic electronics due to the electronic properties induced by their periphery. However, the synthetic access to these compounds remains virtually unexplored. There is a lack in efficient and mild strategies origins in the reduced stability, increased reactivity, and low solubility of these compounds. Herein we report a facile access to pristine zig-zag nanographenes, utilizing an acid-promoted intramolecular reductive cyclization of arylaldehydes, and demonstrate a three-step route to nanographenes constituted of angularly fused tetracenes or pentacenes. The mild conditions are scalable to gram quantities and give insoluble nanostructures in close to quantitative yields. The strategy allows the synthesis of elusive low bandgap nanographenes, with values as low as 1.62 eV. Compared to their linear homologues, the structures have an increased stability in the solid-state, even though computational analyses show distinct diradical character. The structures were confirmed by X-ray diffraction or scanning tunneling microscopy.
Authors with CRIS profile
Dominik Lungerich
Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope
Olena Papaianina
Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope
Mikhail Feofanov
Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope
Jia Liu
Sonderforschungsbereich 953/3 Synthetische Kohlenstoffallotrope
Mirunalini Devarajulu
Professur für Experimentalphysik (Rastersondenmikroskopie)
Sabine Maier
Professur für Experimentalphysik (Rastersondenmikroskopie)
Konstantin Amsharov
Naturwissenschaftliche Fakultät
Involved external institutions
Russian Federation (RU)How to cite
APA:
Lungerich, D., Papaianina, O., Feofanov, M., Liu, J., Devarajulu, M., Troyanov, S.,... Amsharov, K. (2018). Dehydrative pi-extension to nanographenes with zig-zag edges. Nature Communications, 9. https://doi.org/10.1038/s41467-018-07095-z
MLA:
Lungerich, Dominik, et al. "Dehydrative pi-extension to nanographenes with zig-zag edges." Nature Communications 9 (2018).
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