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Keywords:

  • aggregation;
  • gel permeation chromatography;
  • heterocycles;
  • hydrogen bonds;
  • self-assembly

Abstract

The preorganization of bifunctional 2-ureido-4-pyrimidinones mediated by either 1,3-substituted adamantane or meta-substituted phenylene ring linkers leads to the preferred formation of stable pentameric (1)5 and hexameric (2)6 assemblies, respectively. Despite the high binding constant of the 2-ureido-4-pyrimidinone dimers and the highly preorganized structure of the monomer, the predominant formation of cycles (1)5 and (2)6 in solution occurs only within a specific concentration range.