A practical general method for the preparation of long acenes

Andrej Jancarik 1 Gaspard Levet 1 André Gourdon 1
1 CEMES-GNS - Groupe NanoSciences
CEMES - Centre d'élaboration de matériaux et d'études structurales
Abstract : The field of long acenes, the narrowest of the zigzag graphene nanoribbons, has been an area of significant interest in the past decade due to potential applications in organic electronics, spintronics and plasmonics. However their low solubility and high reactivity has so far hindered their preparation on large scales. We report here a concise strategy for the synthesis of higher acenes through Diels-Alder condensation of arynes with a protected tetraene ketone. After deprotection by cleavage of the ketal, the obtained monoketone precursors cleanly yield the corresponding acenes through quantitative cheletropic thermal decarbonylation in the solid state, at moderate temperatures of 155 to 205 °C. This approach allows the preparation of heptacene, benzo[a]hexacene, cis-and trans-dibenzopentacene and offers a valuable new method for the synthesis of even larger acenes.
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Andrej Jancarik, Gaspard Levet, André Gourdon. A practical general method for the preparation of long acenes. Chemistry - A European Journal, Wiley-VCH Verlag, inPress, ⟨10.1002/chem.201805975⟩. ⟨hal-01961616⟩



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