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

Abstract

Synthesis, electronic properties and packing modes of conjugated systems based on 2,5-di(cyanovinyl)furan or thiophene and imino-perfluorophenyl moieties † ‡ Chady Moussallem, Magali Allain, Fre ´de ´ric Gohier and Pierre Fre `re*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, p-p stacking and donor-acceptor interactions. Both structures reveal similar p-stacking of the molecules with nevertheless a more compact packing mode for the furan derivative. Moreover this structure is stabilized by several FÁ Á ÁF interactions between the columns of molecules. By contrast for the thiophene derivative, the structure requires the insertion of CH 2 Cl 2 to be stabilized via ClÁ Á ÁF interactions.

One step synthesis of D-A-D chromophores as active materials for organic solar cells by basic condensation

“…Recently several papers have discussed the key issues regarding the future industrial production of OSCs and underlined the necessity to limit the overall economic cost and environmental impact of the synthesis of active materials while taking care of the possibility of up-scaling the syntheses [4]. Some recent works have demonstrated the possibility of synthesizing D-A or D-A-D systems by means of more environmental friendly methods such as click chemistry [5] or basic condensations [6]. Additionally, the two-fold condensation of aromatic aldehydes onto commercial (Z)-2,3-diaminomaleonitrile to form D-A-D compounds with a central diiminofumaronitrile electro-deficient group has been scantly studied and most articles have been focused on the optical [7] or aggregative [8] properties of the compounds.…”

Fluorine–fluorine type II versus πF–π stacking interactions in the supramolecular organizations of extended thiophene derivatives end capped by imino-perfluorophenyl units

“…We have reported on the structural features of Donor-AcceptorDonor type conjugated materials associating furan or thiophene cycles linked via azomethine bonds to pentafluorophenyl units [28,29]. We showed that the imino-perfluorophenyl units drive the packing modes in the solids via subtle balance between pÀp and donor-acceptor interactions.…”

Synergistic effects of halogen bond and π–π interactions in thiophene-based building blocks

“…Although recognized as a signicant force in improving the packing of many halogen-containing organic compounds, [9][10][11][12] halogen bonding (XB) has been scarcely investigated within "bottom-up" approaches towards organic devices. [13][14][15][16] Halogen bonds, analogues of hydrogen bonds, are non-covalent interactions between Lewis acidic halogen atoms and electron-pairdonating heteroatoms. 17 The phenomenon is explained by the presence of a region of positive electrostatic potential (i.e., shole) on the outermost surface of the halogen atom.…”