Topochemical, Single-Crystal-to-Single-Crystal [2+2] Photocycloadditions Driven by Chalcogen-Bonding Interactions - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2022

Topochemical, Single-Crystal-to-Single-Crystal [2+2] Photocycloadditions Driven by Chalcogen-Bonding Interactions

Résumé

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 center dot center dot center dot Se distance in 1-3 (3.22-3.24 angstrom), a consequence of a strong intramolecular ChB interaction, expands to 3.52-3.54 angstrom in the chalcogen-bonded adducts with bpen, a distance (<4 angstrom) well adapted to the face-to-face association of the bpen molecules into the reactive position toward photochemical dimerization.

Domaines

Chimie organique
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Dates et versions

hal-03772744 , version 1 (10-10-2022)

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Citer

Jan Alfuth, Olivier Jeannin, Marc Fourmigué. Topochemical, Single-Crystal-to-Single-Crystal [2+2] Photocycloadditions Driven by Chalcogen-Bonding Interactions. Angewandte Chemie International Edition, 2022, 61 (36), pp.e202206249. ⟨10.1002/anie.202206249⟩. ⟨hal-03772744⟩
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