“Click” Chemistry in a Supramolecular Environment: Stabilization of Organogels by Copper(I)-Catalyzed Azide−Alkyne [3 + 2] Cycloaddition

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Abstract
Organogels are thermoreversible, viscoelastic (soft) materials consisting of low molecular weight compounds which self-assemble into fibers, often of micrometer lengths and nanometer diameters. The installation of terminal azide and alkyne functional groups on the end of a standard alkylamide-based organogelator was found to cause a modest disruption in the gelation properties of the molecule. Cross-linking of those groups by the copper(I)-catalyzed azide−alkyne cycloaddition reaction produced thermoreversible materials of substantially greater gelation temperatures and mechanical rigidity. These results highlight the ability of azides and alkynesparticipants in the most commonly used “click” reactionto function as innocuous precursors to meaningful covalent interactions in materials science.