Triazolyl-based molecular gels as ligands for autocatalytic ‘click’reactions

Abstract

The catalytic performance of triazolyl-based molecular gels was investigated in the Huisgen 1,3-dipolar cycloaddition of alkynes and azides. Low-molecular-weight gelators derived from l-valine were synthesized and functionalized with a triazole fragment. The resultant compounds formed gels either with or without copper, in a variety of solvents of different polarity. The gelators coordinated CuI and exhibited a high catalytic activity in the gel phase for the model reaction between phenylacetylene and benzylazide. Additionally, the gels were able to participate in autocatalytic synthesis and the influence of small structural changes on their performance was observed.