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A Straightforward Electroactive π-Extended Tetrathiafulvalene (exTTF) Building Block

Authors

  • Agustín Molina-Ontoria,

    1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: +34-913-944-103
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  • Raúl García,

    1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: +34-913-944-103
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  • Andreas Gouloumis,

    1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: +34-913-944-103
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  • Francesco Giacalone,

    1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: +34-913-944-103
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  • M. Rosario Torres,

    1. CAI Difracción de Rayos-X, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain
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  • Nazario Martín

    1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, 28040 Madrid, Spain, Fax: +34-913-944-103
    2. IMDEA – Nanociencia, Campus de Cantoblanco, Universidad Autónoma de Madrid, 28049 Madrid, Spain
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  • Dedicated to Professor Miguel Angel Miranda on the occasion of his 60 birthday

Abstract

The synthesis and X-ray structure of a new and readily available exTTF derivative (6) bearing a methyltriphenylphosphonium bromide moiety as a new building block for the construction of electroactive molecules is reported. The phosphonium salt 6, which was prepared in one step from 2-hydroxymethyl-exTTF as a stable yellow solid in 84 % yield, efficiently undergoes Wittig olefination reactions with a variety of aldehydes to predominantly form the E isomer. Electronic spectra and cyclic voltammetry of the novel compounds reveal the electronic communication between the electroactive units.

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