Core carbo‐mer of an Extended Tetrathiafulvalene: Redox‐Controlled Reversible Conversion to a carbo‐Benzenic Dication

Publikation: Bidrag til tidsskriftLetterfagfællebedømt

  • Dymytrii Listunov
  • Hammerich, Ole
  • Irving Caballero‐quintana
  • Albert Poater
  • Cécile Barthes
  • Carine Duhayon
  • Mie Højer Larsen
  • José‐luis Maldonado
  • Gabriel Ramos‐ortiz
  • Nielsen, Mogens Brøndsted
  • Valérie Maraval
  • Remi Chauvin
carbo‐Benzene is an aromatic molecule devised by inserting C2 units within each C−C bond of the benzene molecule. By integrating the corresponding carbo‐quinoid core as bridging unit in a π‐extended tetrathiafulvalene (exTTF), it is shown that a carbo‐benzene ring can be reversibly formed by electrochemical reduction or oxidation. The so‐called carbo‐exTTF molecule was thus experimentally prepared and studied by UV–visible absorption spectroscopy and cyclic voltammetry, as well as by X‐ray crystallography and by scanning tunneling microscopy (STM) on a surface of highly oriented pyrolytic graphite (HOPG). The molecule and its oxidized and reduced forms were subjected to a computational study at the density functional theory (DFT) level, supporting carbo‐aromaticity as a driving force for the formation of the dication, radical cation, and radical anion. By allowing co‐planarity of the dithiolylidene rings and carbo‐quinoidal core, carbo‐exTTFs present a promising new class of redox‐active systems.
OriginalsprogEngelsk
TidsskriftChemistry: A European Journal
Vol/bind26
Udgave nummer47
Sider (fra-til)10707-10711
Antal sider6
ISSN0947-6539
DOI
StatusUdgivet - 2020

ID: 245709392