We report the difunctional modification of an anionic cobalta bis(dicarbollide)(1-) cluster with a B(8,8')-oxygen bridging unit that provides structural rigidity and an organic alkylazide substituent(s) on the carbon atoms of the metallacarborane cage. These ions present a good binding motif for incorporation into organic molecules using Huisgen-Sharpless (2+3) cycloaddition reactions. In addition, the compounds are chiral, as verified by separation of enantiomers using HPLC on chiral stationary phases (CSPs) and provide a high electrochemical peak in the window located outside of typical signals of biomolecules.