Click-derived supramolecular vesicular nanocatalyst for successive click reactions in water

Abstract

A supramolecular vesicular nanocatalyst (VC) for successive CuI-catalyzed azide–alkyne cycloaddition in water was developed by self-assembly of a click chemistry-derived rod amphiphile (CA). The CA generated by click reaction of azide-terminated benzyl ether dendrons and diethynyl naphthalene self assembles into vesicles in water. The excellent catalytic activity of the VC for click reaction of benzyl azide with phenylacetylene or trimethylsilylacetylene was endowed by CuI-chelation to triazole-containing rod block within VC wall. The products self-encapsulated in VC wall, affecting the interfacial curvature of VC according to their structural compatibility with CA and inducing increase in vesicular size or structural change to micelle. Interestingly, the morphology of VC-derived nanocatalyst was further controlled from micelle to vesicle and vice versa by successive click reactions. The recyclable catalytic activity was visually confirmed by fluorescent changes of the VC solution.