Publications Repository - Gdańsk University of Technology

The face-to-face association of (E)-1,2-di(4-pyridyl)ethylene (bpen) molecules into rectangular motifs stabilized for the first time by chalcogen bonding (ChB) interactions is shown to provide photoreactive systems leading to cyclobutane formation through single-crystal-to-single-crystal [2+2] photodimerizations. The chelating chalcogen bond donors are based on original aromatic, ortho-substituted bis(selenocyanato)benzene derivatives 1–3, prepared from ortho-diboronic acid bis(pinacol) ester precursors and SeO2 and malononitrile in 75–90% yield. The very short intramolecular Se···Se distance in 1–3 (3.22–3.24 Å), a consequence of a strong intramolecular ChB interaction, expands to 3.52–3.54 Å in the chalcogen-bonded adducts with bpen, a distance (< 4 Å) well adapted to the face-to-face association of the bpen molecules into reactive position toward photochemical dimerization.

Authors

• dr inż. Jan Alfuth link open in new tab ,
• Olivier Jeannin,
• Marc Fourmigué