The water-processable nanoreactors are increasingly investigated for catalytic application in order to develop the environment-friendly catalyst working in benign solvent. Especially, supramolecular nanoreactors are of great interest as it can be used as molecular catalysts having a large quantity of catalytically active nanoparticles within the nanostructure. Meanwhile, “Click chemistry” has been widely used to develop new materials by allowing to link together two molecular fragments with synthetic simplicity, mild reaction condition, fast and quantitative reaction. Interestingly, the resulting Click-derived triazole group plays a role as a ligand for chelating metal ion with specific binding affinity depending on the triazole-containing molecular structure. In this work, triazole-based amphiphilic molecules containing aromatic and hydrophilic tri(ethylene oxide) segment were easily synthesized using facile Click chemistry. Moreover, it revealed the Cu2+-binding process by the triazole group of the amphiphiles which leads to the formation of nano-aggregates even below the critical micellar concentration (CMC). The Cu2+-nanoassemblies can be a facile nanocatalyst for activating the azide-alkyne cycloaddition in aqueous medium by reduction of the Cu2+ to Cu+. The interesting point is that “Click chemistry” can induce another Click reaction in water based on supramolecular nanostructure and further, the Click-derived products could control the vesicular size of nanoreactor depending on the coplanarity and bulkiness of the products. Thus, the Cu2+-amphiphile conjugates can provide a useful and simple strategy for the fabrication of the self-assembled nanoreactor as well as detection of metal ions in aqueous medium.

Click chemistry-derived aqueous supramolecular nanoreactors based on amphiphilic molecules

251st National Meeting (2016)

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