Versatile one-pot synthesis of supramolecular plastics and self-healing rubbers

J Am Chem Soc. 2009 Jun 17;131(23):7966-7. doi: 10.1021/ja903080c.

Abstract

We propose a strategy to obtain through a facile one-pot synthesis a large variety of supramolecular materials that can behave as differently as associating low-viscosity liquids, semicrystalline or amorphous thermoplastics, viscoelastic melts or rubbers. Such versatility is achieved thanks to simultaneous synthesis of branched backbones and grafting of associating units. This contrasts with usual synthetic pathways that rely on grafting functional groups on preprepared backbones. We use oligocondensation of fatty di- and triacids with diethylenetriamine and finely tune the molecular weight and degree of branching by end-capping some acid groups before condensation by reaction with aminoethylimidazolidone. Supramolecular assembly is formed thanks to complementary and self-complementary associations of amide, imidazolidone, and dialkylurea groups, and the stoichiometry directly controls the mesoscopic structure and properties.