Dehydrative π-extension to nanographenes with zig-zag edgesстатья
Статья опубликована в высокорейтинговом журнале
Информация о цитировании статьи получена из
Web of Science,
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Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 26 декабря 2018 г.
Аннотация: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.