A multi-component CuAAC 'click' approach to an exo functionalised pyridyl-1,2,3-triazole macrocycle: Synthesis, characterisation, Cu(I) and Ag(I) complexes

A one-pot, multi-component CuAAC reaction was exploited for the safe generation of an exo alcohol-functionalised pyridyl-1,2,3-triazole click macrocycle in good yield. The macrocycle was characterised by elemental analysis, HR-ES-MS, ¹H and ¹³C NMR spectrometry, and the molecular structure was confirmed by X-ray crystallography. Efforts to use the click macrocycle in both passive and active metal template syntheses of [2]rotaxanes were unsuccessful, and this appears to be connected to the coordinating ability of the 1,2,3-triazole units in the macrocycle. The coordination chemistry of the macrocycle with Cu(I) and Ag(I) was examined. It has been demonstrated using HR-ES-MS, ¹H NMR spectrometry and X-ray crystallography that the macrocycle can form both discrete and polymeric coordination compounds with Cu(I) and Ag(I) and in all cases the 1,2,3-triazolyl units of the macrocycle are coordinated to the metal ions.