Triazolyl-Based Molecular Gels as Ligands for Autocatalytic 'Click' Reactions

Chemistry. 2016 Jun 13;22(25):8676-84. doi: 10.1002/chem.201600594. Epub 2016 May 11.

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 Cu(I) 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.

Keywords: click chemistry; gels; heterogeneous catalysis; self-assembly; supramolecular chemistry.