Size‐Control by Anion Templating in Mechanochemical Synthesis of Hemicucurbiturils in the Solid State

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Abstract
Self‐organization is one of the most intriguing phenomena of chemical matter. While the self‐assembly of macrocycles and cages in dilute solutions has been extensively studied, it remains poorly understood in solvent‐free environments. Provided here is the first example of using anionic templates to achieve selective assembly of differently‐sized macrocycles in a solvent‐free system. Using acid‐catalyzed synthesis of cyclohexanohemicucurbiturils as a model, size‐controlled, quantitative synthesis of 6‐ or 8‐membered macrocycles by spontaneous anion‐directed reorganization of mechanochemically‐made oligomers in the solid state is demonstrated.
Funding Information
  • National sciences and engineering research council (RGPIN-2017-06467, NSERC SMFSU 507347-17)
  • Estonian Ministry of Education and Research (IUT 19-32, PUT692)
  • Centre of Excellence in Molecular Cell Engineering (2014-2020.4.01.15-0013)
  • European Regional Development Fund Dora Pluss

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