Synthesis of self-assembling glycerotriazolophanes

Twenty 16-membered triazole-based macrocycles possessing different pseudo-symmetry elements have been synthesized using the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The formation of the macrocycles was accompanied by their spontaneous self-assembly leading to solids with distinct layered structures as confirmed by scanning electron microscopy. The self-assembling properties of the product and the "on water" reaction media seemed to form the driving force for the reaction in a t-butanol-water system. The self-assembling properties of these macrocycles was supported by quantum chemical studies using Density Functional Theory.