2-Iodo-1,6-dithiapyrene: Syntheses, crystal structures and physical properties of CT complexes and salt

2-Iodo-1,6-dithiapyrene (IDTPY) was designed and synthesized as a new electron-donor molecule with halogen-bonding functionality, and possesses an adequate solubility and a moderate electron-donating ability comparable to that of ethylenedithio-tetrathiafulvalene. IDTPY formed a two-dimensional sheet structure through strong I⋯S and weak S⋯S interactions in the crystal. The DDQ, cyananilic acid, nitranilic acid (H2NRAL) complexes and NO3- salt of IDTPY have been newly synthesized. In the crystals of H2NRAL complex and NO3- salt of IDTPY, there are dimeric structures of IDTPY+ and intermolecular I⋯O contacts between IDTPY and NRAL2− or NO3-. The room temperature electric conductivities of their CT complexes and salt were 1.5 × 10−2–7.3 × 10−6 S cm−1.

New charge-transfer complexes and salt of 2-iodo-1,6-dithiapyrene (IDTPY) with DDQ, cyananilic acid, nitranilic acid (H2NRAL), and nitrate were prepared, and their physical properties were investigated by optical and electric conductivity measurements. In the crystals of H2NRAL complex and nitrate salt, dimeric structures of IDTPY and short I⋯O contacts were formed.Figure optionsDownload as PowerPoint slide