Abstract The synthesis of novel Cookson’s birdcage-annulated thiacrowns as well as noncage oligomers with an incorporated 1,2,3-triazole moiety are described. The title compounds were prepared applying a click alkyne–azide cycloaddition reaction in the final macrocyclization step. Using this methodology a series of oligomers containing oxygen, nitrogen, and sulfur were prepared. The effective cycloaddition