The reaction of alkyne and azide groups to form a covalent linkage through �click� chemistry is widely used to derivatize and label a variety of targets, from metal surfaces to biomolecules. We are investigating the utility of 7-octyne-2,4-dione as a propargyl-bearing �-diketone to coordinate transition metals directly, as well as its incorporation in Schiff base ligands of the �acacen� type. We have found that the reported synthesis and purification of this particular propargylated acetylacetone to be straightforward, and have used it to make an acacen-type ligand. We have also investigated a variant bearing a propargyl group at the middle carbon of acetylacetone. We have characterized these compounds using NMR and GC-MS and are using them to modify gold surfaces bearing ?-azidoalkanethiols. The modified electrodes have been treated with a variety of metal cations (cobalt, manganese, vanadyl) to provide different electrochemical reponses.

Use of a metal-coordinating diketone bearing a propargyl group in “click” chemistry

243rd National Meeting (2012)

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