Centre d’Élaboration de Matériaux et d’Etudes Structurales (UPR 8011)


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Oligoacenes

Synthesis of acenes beyond pentacene

The field of long acenes, the narrowest of the zig-zag 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.

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We have designed a concise strategy for the synthesis of higher acenes through Diels-Alder condensation of arynes (step a) with a protected tetraene ketone 1. After deprotection by cleavage of the ketal (step b), the obtained monoketone precursors cleanly yield the corresponding acenes through quantitative cheletropic thermal decarbonylation in the solid state (step c), at moderate temperatures of 155 to 205 °C. This approach allows the preparation of heptacene 2, benzo[a]hexacene 3, cis- and trans-dibenzopentacene 4/5 and offers a valuable new method for the synthesis of even larger acenes.

 

Référence

A practical general method for the preparation of long acenes. A. Jancarik, G. Levet, A. Gourdon, Chem. Eur. J. 2019, 25, 2366 – 2374

Funding

Europe : PAMS (FET), ORQUID (Quantera), PASIMOD (Sea of Excellence)