Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties - Université d'Angers Accéder directement au contenu
Article Dans Une Revue New Journal of Chemistry Année : 2013

Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties

Chady Moussallem
  • Fonction : Auteur
Magali Allain
Frédéric Gohier
Pierre Frère

Résumé

The synthesis, the electronic properties and the solid state arrangements of conjugated systems associating pentafluorophenyl units linked via azomethine bonds to a central 2,5-di(cyanovinyl)-thiophene or furan moieties have been investigated. The crystal structures of the two compounds are analyzed in terms of intermolecular interactions involving hydrogen and halogen bonding, pi-pi stacking and donor-acceptor interactions. Both structures reveal similar pi-stacking of the molecules with nevertheless a more compact packing mode for the furan derivative. Moreover this structure is stabilized by several F center dot center dot center dot F interactions between the columns of molecules. By contrast for the thiophene derivative, the structure requires the insertion of CH2Cl2 to be stabilized via Cl center dot center dot center dot F interactions.

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Dates et versions

hal-03344592 , version 1 (15-09-2021)

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Chady Moussallem, Magali Allain, Frédéric Gohier, Pierre Frère. Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties. New Journal of Chemistry, 2013, 37 (2), pp.409-415. ⟨10.1039/c2nj40745k⟩. ⟨hal-03344592⟩
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