Dehydrative π-extension to nanographenes with zig-zag edges

Dominik Lungerich, Olena Papaianina, Mikhail Feofanov, Jia Liu, Mirunalini Devarajulu, Sergey I. Troyanov, Sabine Maier and Konstantin Amsharov ()
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Dominik Lungerich: Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg
Olena Papaianina: Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg
Mikhail Feofanov: Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg
Jia Liu: Department of Physics, Friedrich-Alexander-University Erlangen-Nuernberg
Mirunalini Devarajulu: Department of Physics, Friedrich-Alexander-University Erlangen-Nuernberg
Sergey I. Troyanov: Chemistry Department, Moscow State University
Sabine Maier: Department of Physics, Friedrich-Alexander-University Erlangen-Nuernberg
Konstantin Amsharov: Department of Chemistry and Pharmacy, Organic Chemistry II, Friedrich-Alexander-University Erlangen-Nuernberg

Nature Communications, 2018, vol. 9, issue 1, 1-8

Abstract: 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.

Date: 2018
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DOI: 10.1038/s41467-018-07095-z

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