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

Jan Alfuth; Olivier Jeannin; Marc Fourmigué

doi:10.1002/anie.202206249

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

Abstract

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.

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Authors (3)

Jan Alfuth dr inż.
Olivier Jeannin
- Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)
Marc Fourmigué
- Univ Rennes, CNRS, ISCR (Institut des Sciences Chimiques de Rennes)

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Articles

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artykuły w czasopismach

Published in:

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION no. 61,
ISSN: 1433-7851

Language:

English

Publication year:

2022

Bibliographic description:

Alfuth J., Jeannin O., Fourmigué M.: Topochemical, Single‐Crystal‐to‐Single‐Crystal [2+2] Photocycloadditions Driven by Chalcogen‐Bonding Interactions// ANGEWANDTE CHEMIE-INTERNATIONAL EDITION -Vol. 61,iss. 36 (2022),

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