Structurally rigidified cobalt bis(dicarbollide) derivatives, a chiral platform for labelling of biomolecules and new materials

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.

Automated summary

In this study, we have reported a difunctional modification method for anionic cobalta bis(dicarbollide)(1(-)) clusters by introducing a B(8,8')-oxygen bridging unit and organic alkylazide substituents on the carbon atoms of the metallacarborane cage, which enhances their structural rigidity. These ions show good binding motifs for incorporation into organic molecules through Huisgen-Sharpless (2+3) cycloaddition reactions, and can be separated into enantiomers using chiral stationary phases. The electrochemical testing results indicate that these compounds exhibit high peaks located outside the typical signals of biomolecules.