Electrochemical illumination of intramolecular communication in ferrocene-containing tris -β-diketonato aluminum(III) complexes; Cytotoxicity of Al(FcCOCHCOCF 3) 3

Henno J. Gericke, Alfred J. Muller, Jannie C. Swarts

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26 Citations (Scopus)

Abstract

The series of ferrocene-containing tris-β-diketonato aluminum(III) complexes [Al(FcCOCHCOR) 3] (R = CF 3, 1; CH 3, 2; C 6H 5, 3; and Fc = ferrocenyl = Fe(η 5- C 5H 5)(η 5-C 5H 4), 4) were synthesized and investigated structurally and electrochemically; complex 1 was subjected to cytotoxicity tests. 1H NMR-spectroscopy distinguished between the mer and fac isomers of 2 and 3. Complex 1 existed only as the mer isomer. A single crystal X-ray crystallographic determination of the structure of a mer-isomer of Al(FcCOCHCOCF 3) 3, 1, (Z = 4, space group P2 12 12 1) demonstrated extensive delocalization of all bonds which explained the pronounced electrochemically observed intramolecular communication between molecular fragments. In contrast to electrochemical studies in CH 2Cl 2/[N( nBu) 4][PF 6], the use of the supporting electrolyte [N( nBu) 4][B(C 6F 5) 4] allowed identification of all Fc/Fc + electrochemical couples by cyclic and square wave voltammetry for 1-4. For R = Fc, formal reduction potentials of the six ferrocenyl groups were found to be E°′ = 33, 123, 304, 432, 583, and 741 mV versus free ferrocene respectively. Complex 1 (IC 50 = 10.6 μmol dm -3) was less cytotoxic than the free FcCOCH 2COCF 3 ligand having IC 50 = 6.8 μmol dm -3 and approximately 2 orders of magnitude less toxic to human HeLa neoplastic cells than cisplatin (IC 50 = 0.19 μmol dm -3).

Original languageEnglish
Pages (from-to)1552-1561
Number of pages10
JournalInorganic Chemistry
Volume51
Issue number3
DOIs
Publication statusPublished - 6 Feb 2012

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

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