Self-Assembled Copper Metallogel Bearing Terpyridine and Its Application as a Catalyst for the Click Reaction in Water.

Abstract

Metallogels have attracted a great deal of interest because of their intriguing properties and applications in chemsensors, batteries, catalysis, and other fields. In this work, a novel ligand bearing terpyridine and hydroxyamine units was designed and synthesized. The ligand selectively gelated with copper ions in water by heating and cooling or sonication. Different physicochemical studies [Fourier transform infrared, ultraviolet-visible (UV-vis), electron paramagnetic resonance (EPR), scanning electron microscopy, X-ray diffraction, and rheology] were conducted to characterize the gels. We show that coordination interaction, π-π interaction, and noncovalent interaction had obvious effects on the properties of the gel. Additionally, a stable radical hydrogel could be obtained by ultrasound treatment, which was accompanied by color variation from green to blue. This was further confirmed by UV-vis and EPR experiments. Furthermore, the copper metallogels were developed as catalysts for the preparation of 1,2,3-triazole derivatives in water at 25 °C. Although various types of catalysts have been investigated, the use of metallogels as catalysts for the click reaction in water has been scarce. This strategy shows the process is simple, affords a high yield, and is "green" and economical.