Synthesis of ferrocenyl based β‑hydroxy-1,2,3- triazoles and study of electrochemical properties via click reaction

Abstract

A series of ferrocenyl-based β‑hydroxy-1,2,3-triazole derivatives were synthesized from a reaction between ferrocenyl-based β‑hydroxy azide derivatives and some terminal alkynes such as phenylacetylene, propargyl alcohol, and (2-propynyloxy) alkylferrocenes through the click reaction under CuI as catalyst. Ferrocenyl-based β‑hydroxy azides were synthesized from ring-opening reaction of ferrocenyl-based glycidyl ethers with sodium azide in the mixture of water and methanol and ammonium chloride as catalyst. Ferrocenyl-based glycidyl ethers derivatives were synthesized via a reaction of epichlorohydrin with 4-ferrocenylbutanol and 3-ferrocenylpropanol in the presence of NaOH and tetrabutylammonium iodide as phase transfer catalyst. Structures of synthesized compounds were elucidated by common spectroscopy techniques such as FT-IR, 1H NMR, and 13C NMR and CHN elemental analysis. Electrochemical and optical properties of these ferrocenyl-based derivatives were studied by cyclic voltammetry and UV–Visible experiments, respectively.