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The Tris-Urea Motif and Its Incorporation into Polydimethylsiloxane-Based Supramolecular Materials Presenting Self-Healing Features

Authors

  • Dr. Nabarun Roy,

    1. Laboratoire de Chimie Supramoléculaire, ISIS, Université de Strasbourg, 8, allée Gaspard Monge, 67000, Strasbourg (France), Fax: (+33) 368-855140
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  • Prof. Eric Buhler,

    1. Laboratoire de Chimie Supramoléculaire, ISIS, Université de Strasbourg, 8, allée Gaspard Monge, 67000, Strasbourg (France), Fax: (+33) 368-855140
    2. Matière et Systèmes Complexes, Université Paris Diderot-Paris 7, 10, rue Alice Domon et Léonie Duquet, 75205 Paris Cedex 13 (France)
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  • Prof. Jean-Marie Lehn

    Corresponding author
    1. Laboratoire de Chimie Supramoléculaire, ISIS, Université de Strasbourg, 8, allée Gaspard Monge, 67000, Strasbourg (France), Fax: (+33) 368-855140
    • Laboratoire de Chimie Supramoléculaire, ISIS, Université de Strasbourg, 8, allée Gaspard Monge, 67000, Strasbourg (France), Fax: (+33) 368-855140
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Abstract

Materials of supramolecular nature have attracted much attention owing to their interesting features, such as self-reparability and material robustness, that are imparted by noncovalent interactions to synthetic materials. Among the various structures and synthetic methodologies that may be considered for this purpose, the introduction of extensive arrays of multiple hydrogen bonds allows for the formation of supramolecular materials that may, in principle, present self-healing behavior. Hydrogen bonded networks implement dynamic noncovalent interactions. Suitable selection of structural units gives access to novel dynamic self-repairing materials by incrementing the number of hydrogen-bonding sites present within a molecular framework. Herein, we describe the formation of a tris-urea based motif giving access to six hydrogen-bonding sites, easily accessible through reaction of carbohydrazide with an isocyanate derivative. Extension towards the synthesis of multiply hydrogen-bonded supramolecular materials has been achieved by polycondensation of carbohydrazide with a bis-isocyanate component derived from poly-dimethylsiloxane chains. Such materials underwent self-repair at a mechanically cut surface. This approach gives access to a broad spectrum of materials of varying flexibility by appropriate selection of the bis-isocyanate component that forms the polymer backbone.

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