Molecular "Building Block" and "Side Chain Engineering": Approach to Synthesis of Multifunctional and Soluble Poly(pyrrole phenylene)s

Abstract

Here, the synthesis of a novel poly(pyrrole phenylene) (PpyP) that is both modular in ways of functionalization and soluble in organic solvents is reported, and therefore solution processable. This is achieved through the functionalization of the side-chain substituents in pyrrole phenylene (PyP) repeating units. ^t Butyl acrylate brushes are first grafted through atom transfer radical polymerization from one type of PyP, followed by oxidative chemical co-polymerization of the grafted PyP with a PyP bearing different side chains-either an azide or a methoxy moiety, resulting in a soluble PpyP where solubility is not dopant-dependent. Successful post-polymerization modification through "click" chemistry and post-polymerization processing via electrospinning are also demonstrated. Additionally, performed computational calculations indicate planarity of the novel polyrrole phenylene monomers and ionisation potentials that favor α-α bond formation during their polymerization.

Keywords: conducting polymers; functionalizations; macromolecules; polypyrroles.