Abstract:A small family of [Co 2 (L pytrz ) 3 ] 6+ cylinders was synthesised from bis(bidentate) 2-pyridyl-1,2,3-triazole "click" ligands (L pytrz ) through an "assembly-followed-by-oxidation" method. The cylinders were characterised using 1 H, 13 C, and DOSY NMR, IR, and UV-Vis spectroscopies, along with electrospray ionisation mass spectrometry (ESMS). Stability studies were conducted in dimethyl sulfoxide (DMSO) and D 2 O. In contrast to similar, previously studied, [Fe 2 (L pytrz ) 3 ] 4+ helicates the more kinetically inert [Co 2 (L pytrz ) 3 ] 6+ systems proved stable (over a period of days) when exposed to DMSO and were even more stable in D 2 O. The triply stranded [Co 2 (L pytrz ) 3 ] 6+ systems and the corresponding "free" ligands were tested for antimicrobial activity in vitro against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) microorganisms. Agar-based disk diffusion and Mueller-Hinton broth micro-dilution assays showed that the [Co 2 (L pytrz ) 3 ] 6+ cylinders were not active against either strain of bacteria. It is presumed that a high charge of the [Co 2 (L pytrz ) 3 ] 6+ cylinders is preventing them from crossing the bacterial cell membranes, rendering the compounds biologically inactive.