Organometallic–Inorganic Conjugated Unsymmetrical Schiff-Base Hybrids. Synthesis, Characterization, Electrochemistry and X-ray Crystal Structures of Functionalized Trinuclear Iron–Nickel–Ruthenium Dipolar Chromophores

  • Alexander Trujillo
  • Sourisak Sinbandhit
  • Loïc Toupet
  • David Carrillo
  • Carolina Manzur
  • Jean-René Hamon
Article
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Abstract

The synthesis of neutral dinuclear iron–nickel unsymmetrical Schiff base complexes 3 and 4 was achieved via a template reaction involving equimolar amounts of alkyl or aryl “half-unit” precursors, respectively, Fc–C(O)CH=C(CH3)N(H)R (1: R = CH2CH2NH2; 2: R = o-C6H4NH2; Fc = CpFe(η5-C5H4); Cp = η5-C5H5), 5-bromosalicylaldehyde and nickel(II) acetate tetrahydrate in a refluxing CH2Cl2/MeOH (1:1) mixture. The ionic trinuclear unsymmetrical complex 5 was prepared by reacting its dinuclear precursor 3 with the arenophile source, [Cp*Ru(NCCH3)3]PF6 (Cp* = η5-C5(CH3)5), in refluxing CH2Cl2 for 2 h, whereas the trinuclear species 6 was formed upon regioselective π-complexation of the 5-bromosalicylidene ring of 4 by [Cp*Ru]+ at room temperature overnight. All the new compounds were adequately characterized by analytical and spectroscopic techniques and, in addition, the crystal and molecular structures of the “half-unit” 1, the binuclear complex 4 and its hemisolvate adduct 4 · 0.5CH3OH, the trinuclear Schiff base compound 5 · 2(CH3)2CO, and the mixed sandwich metalloligand 7 have been determined by X-ray crystallography. Both organometallic–inorganic hybrids 5 and 6 contain the neutral electron-releasing ferrocenyl group, and the cationic electron-withdrawing ruthenium mixed sandwich, linked through the unsymmetrical tetradentate Schiff base complex {Ni(ONNO)}. UV–vis, 1H and 13C NMR as well as electrochemical data clearly indicate a mutual donor–acceptor electronic influence between the organometallic termini. Furthermore, X-ray crystal structure analysis of 5 · 2(CH3)2CO reveals the partial delocalization of bonding electron density throughout the dinucleating nickel Schiff base ligand.

Keywords

Ferrocenyl ketoamine Unsymmetrical Schiff base complexes Push-pull complexes Trinuclear iron–nickel–ruthenium complexes Crystal structure 
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Notes

Acknowledgements

The authors gratefully acknowledge Dr. B. Demerseman (Rennes) for a generous gift of [Cp*Ru(NCCH3)3]PF6. Thanks are also addressed to Dr. P. Jéhan (CRMPO, Rennes) for invaluable assistance with mass spectrometric measurements. Financial support from the Fondo Nacional de Desarrollo Científico y Tecnológico [FONDECYT (Chile); Grant No. 1040851 (C. M. and D. C.)], the ECOS-SUD (France)—CONICYT (Chile) agreement No. C05E03 (C. M., D. C. and J.-R. H.), and the Pontificia Universidad Católica de Valparaíso, Chile (C. M. and D. C.), is gratefully acknowledged. A. T. thanks the CONICYT (Chile) for support of a graduate fellowship.

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Copyright information

© Springer Science+Business Media, LLC 2007

Authors and Affiliations

  • Alexander Trujillo
    • 1
    • 2
  • Sourisak Sinbandhit
    • 3
  • Loïc Toupet
    • 4
  • David Carrillo
    • 1
  • Carolina Manzur
    • 1
  • Jean-René Hamon
    • 2
  1. 1.Laboratorio de Química Inorgánica, Instituto de QuímicaPontificia Universidad Católica de ValparaísoValparaisoChile
  2. 2.UMR 6226 “Sciences Chimiques de Rennes”CNRS-Université de Rennes 1Rennes CedexFrance
  3. 3.Centre Régional de Mesures Physiques de l’OuestUniversité de Rennes 1Rennes CedexFrance
  4. 4.UMR 6626, Groupe Matière Condensée et MatériauCNRS-Université de Rennes 1Rennes CedexFrance

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