Syntheses, crystal structures, and electrochemistry of a series of ferrocene-containing ketoimines

Abstract

Condensation of ferrocenoylacetone with arylamine or benzylamine in toluene at reflux afforded a series of N,O-bidentate ferrocenoyl enaminone ligands, Fc–C(O)CH = C(CH₃)N(H)R¹ (HL1: R¹ = C₆H₅; HL2: R¹ = 4-I-C₆H₄; HL3: R¹ = 4-Cl-C₆H₄; HL4: R¹ = 4-Me-C₆H₄; HL5: R¹ = 4-OMe-C₆H₄; HL6: R¹ = 2-Me-C₆H₄; HL7: R¹ = 2-OMe-C₆H₄; HL8: R¹ = 2-F-C₆H₄; HL9: R¹ = CH₂C₆H₅; Fc = ferrocenyl). Reaction of Cu(CH₃COO)₂ with two equivalents of HL1, HL3, and HL5-HL8 in the presence of CH₃ONa in ethanol gave six copper complexes, [Cu(L1)₂] (1), [Cu(L3)₂] (2), [Cu(L5)₂] (3), [Cu(L6)₂] (4), [Cu(L7)₂] (5) and [Cu(L8)₂] (6), respectively. All compounds were characterized by ¹H NMR, FT-IR, and UV–vis spectroscopies along with their electrochemical properties. The molecular structures of HL1-HL3, HL5, HL6, and HL8, together with the copper complexes 2.0.6C₂H₅OH and 3.CH₃OH have been established by single-crystal X-ray diffraction.

Graphical Abstract

Keywords:

• Ferrocenoyl enaminone ligand
• copper complex
• synthesis
• crystal structure
• electrochemical property

Acknowledgements

This project was supported by Natural Science Foundation of Anhui Province (2008085MB58) and Key projects funded by Anhui Province for the cultivation of outstanding talents in Colleges and Universities (gxyqZD2021105).

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This project was supported by Natural Science Foundation of Anhui Province (2008085MB58) and Key projects funded by Anhui Province for the cultivation of outstanding talents in Colleges and Universities (gxyqZD2021105).