Click reaction in the synthesis of novel thiophosphorylated ligands for electrochemical hydrogen evolution

O-Propargylation of free hydroxyl groups in calix[4]resorcinols bearing thiophosphoryloxyphenyl substituents at the lower rim and possessing cone or chair conformations afforded new derivatives containing eight terminal alkyne groups. Their subsequent click reaction with azidomethylarenes led to the corresponding multifunctional triazole calix[4]resorcinols. Nickel complexes with such ligands show catalytic activity in hydrogen evolution reaction providing the decrease in potential of the direct acid reduction on glassy carbon electrode of 0.98V.