O‐Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed‐Valence Complexes - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2020

O‐Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed‐Valence Complexes

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Luka Ðorđević
  • Fonction : Auteur
Cataldo Valentini
  • Fonction : Auteur
Cécile Mézière
Magali Allain
Marc Salle
Andrea Folli
  • Fonction : Auteur
Damien Murphy
  • Fonction : Auteur
Samuel Mañas‐valero
  • Fonction : Auteur

Résumé

Herein we report an efficient synthesis to prepare O-doped nanographenes derived from the p-extension of pyrene. The derivatives are highly fluorescent and feature low oxidation potentials. Using electrooxidation, crystals of cationic mixedvalence (MV) complexes were grown in which the organic salts organize into face-to-face p-stacks, a favorable solid-state arrangement for organic electronics. Variable-temperature electron paramagnetic resonance (EPR) measurements and relaxation studies suggest a strong electron delocalization along the longitudinal axis of the columnar p-stacking architectures. Electric measurements of single crystals of the MV salts show a semiconducting behavior with a remarkably high conductivity at room temperature. These findings support the notion that p-extension of heteroatomdoped polycyclic aromatic hydrocarbons is an attractive approach to fabricate nanographenes with a broad spectrum of semiconducting properties and high charge mobilities.

Dates et versions

hal-02529207 , version 1 (02-04-2020)

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Citer

Luka Ðorđević, Cataldo Valentini, Nicola Demitri, Cécile Mézière, Magali Allain, et al.. O‐Doped Nanographenes: A Pyrano/Pyrylium Route Towards Semiconducting Cationic Mixed‐Valence Complexes. Angewandte Chemie International Edition, 2020, 59 (10), pp.4106-4114. ⟨10.1002/anie.201914025⟩. ⟨hal-02529207⟩
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