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.
journal_name
Nat Communjournal_title
Nature communicationsauthors
Lungerich D,Papaianina O,Feofanov M,Liu J,Devarajulu M,Troyanov SI,Maier S,Amsharov Kdoi
10.1038/s41467-018-07095-zsubject
Has Abstractpub_date
2018-11-12 00:00:00pages
4756issue
1issn
2041-1723pii
10.1038/s41467-018-07095-zjournal_volume
9pub_type
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