Structurally Diverse Polyamides Obtained from Monomers Derived via the Ugi Multicomponent Reaction

Authors

  • Dr. Oliver Kreye,

    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-46801
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  • Oğuz Türünç,

    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-46801
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  • Ansgar Sehlinger,

    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-46801
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  • Jenny Rackwitz,

    1. Institute of Chemistry, Laboratory for Sustainable Organic Synthesis, University of Potsdam, Karl-Liebknecht-Str. 24–25, 14476 Golm/Potsdam (Germany)
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  • Prof. Dr. Michael A. R. Meier

    Corresponding author
    1. Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-46801
    • Laboratory of Applied Chemistry, Institute of Organic Chemistry, Karlsruhe Institute of Technology, Fritz-Haber-Weg 6, Building 30.42, 76131 Karlsruhe (Germany), Fax: (+49) 721-608-46801
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Abstract

The combination of the Ugi four-component reaction (Ugi-4CR) with acyclic diene metathesis (ADMET) or thiol–ene polymerization led to the formation of poly-1-(alkylcarbamoyl) carboxamides, a new class of substituted polyamides with amide moieties in the polymer backbone, as well as its side chains. 10-Undecenoic acid, obtained by pyrolysis of ricinoleic acid, the main fatty acid of castor oil, was used as the key renewable building block. The use of different primary amines, as well as isonitriles (isocyanides) for the described Ugi reactions provided monomers with high structural diversity. Furthermore, the possibility of versatile post-modification of functional groups in the side chains of the corresponding polymers should be of considerable interest in materials science. The obtained monomers were polymerized by ADMET, as well as thiol–ene, chemistry and all polymers were fully characterized. Finally, ortho-nitrobenzylamide-containing polyamides obtained by this route were shown to be photoresponsive and exhibited a dramatic change of their properties upon irradiation with light.

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