Metal-Free, Multicomponent Synthesis of Pyrrole-Based π-Conjugated Polymers from Imines, Acid Chlorides, and Alkynes

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Abstract
Multicomponent coupling reactions (MCRs) are becoming increasingly used in the synthesis of macromolecules, as they can allow the rapid generation of libraries of materials as a method to tune properties. MCRs could prove particularly useful in the synthesis of π-conjugated polymers, in which structural changes are necessary for fine tuning of electronic properties. We describe here the first metal-free multicomponent approach to conjugated polymers. This reaction exploits the coupling of imines, acid chlorides and (catechyl)PPh to generate phospha-Münchnone containing polymers, which can be converted to poly(pyrroles) via cycloaddition. The platform allows for the efficient synthesis of families of high molecular weight polymers in one step from readily available monomers.
Funding Information
  • Canada Foundation for Innovation
  • Fonds Québécois de la Recherche sur la Nature et les Technologies
  • Natural Sciences and Engineering Research Council of Canada

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