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Utilizing "Latent" Carbon: Repositioning Hydrogen-Bonded Synthons and Assemblies via Halogen Bonding to π-Systems.

Jogirdas VainauskasAlexander Wahrhaftig-LewisTomislav Friščić
Published in: Angewandte Chemie (International ed. in English) (2024)
Molecules bearing carboxylic acid, amide, and hydroxyl groups are ubiquitous in crystal engineering, where robust hydrogen-bonded synthons centred on these functionalities enable reliable crystal structure design. We now show that halogen bonding to the carbon π-system of such molecules, traditionally ignored in crystal engineering, permits the recognition and directional assembly of the resulting hydrogen-bonded structural subunits, leaving the archetypal hydrogen-bonded ring, ladder, and chain homosynthons intact, but repositioned in space. When applied to heteromolecular synthons, this enables rearranging more complex hydrogen-bonded motifs and the evolution of binary cocrystals into ternary ones through "latent" carbon-based recognition sites, demonstrating a rational approach to build higher-order solid-state supramolecular assemblies.
Keyphrases
  • solid state
  • crystal structure
  • visible light
  • reduced graphene oxide