An Original Electrochemical Pathway for the Synthesis of Porphyrin Oligomers

Authors

  • Dr. Delphine Schaming,

    1. Laboratoire de Chimie Physique, UMR 8000 CNRS/Université Paris-Sud 11, Faculté des Sciences d'Orsay, Bâtiment 349, 91405 Orsay cedex (France)
    2. Present address: Laboratoire ITODYS, UMR 7086 CNRS/Université Paris Diderot, -Sorbonne Paris Cité, Bât. Lavoisier, 15 rue Jean-Antoine de Baïf, Case 7107, 75205 Paris Cedex 13 (France)
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  • Dr. Yun Xia,

    1. Laboratoire de Chimie Physique, UMR 8000 CNRS/Université Paris-Sud 11, Faculté des Sciences d'Orsay, Bâtiment 349, 91405 Orsay cedex (France)
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  • Dr. René Thouvenot,

    1. Institut Parisien de Chimie Moléculaire, UMR 7201 CNRS/Université Pierre et Marie Curie (Université Paris 06), Case courrier 42, 4 Place Jussieu, 75252 Paris cedex 05 (France)
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  • Prof. Laurent Ruhlmann

    Corresponding author
    1. Laboratoire de Chimie Physique, UMR 8000 CNRS/Université Paris-Sud 11, Faculté des Sciences d'Orsay, Bâtiment 349, 91405 Orsay cedex (France)
    2. Present address: Laboratoire d'Electrochimie et de Chimie-Physique du Corps Solide, UMR 7177 CNRS/Université de Strasbourg, 4 rue Blaise Pascal, 67081 Strasbourg (France), Fax:(+33) 3-68-85-14-31
    • Laboratoire de Chimie Physique, UMR 8000 CNRS/Université Paris-Sud 11, Faculté des Sciences d'Orsay, Bâtiment 349, 91405 Orsay cedex (France)
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Abstract

An electrosynthesis process has allowed the formation of four oligomers, containing three, four, or five macrocycles. This method is based on the nucleophilic attack of porphyrins substituted by several pendant pyridyl groups to the electrogenerated radical cation of zinc β-octaethylporphyrin (ZnOEP), according to an ECEC processes. Thus, a control of the number of macrocycles and of the geometry of the oligomers can be performed. These new compounds have been characterized by HRMS as well as 1H NMR, UV/Vis, and fluorescence spectroscopy, and electrochemistry. The results show a strong influence of the pyridinium spacers on the macrocycles.

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