 Polymers that can undergo continuous head-to-tail depolymerization in response to a specific signal show promise as stimuli responsive materials for use in medical, environmental, and industrial settings. In this presentation, we describe a new class of depolymerizable poly(benzyl ethers) from stabilized quinone methides. These polymers can be synthesized to give high degrees of polymerization and can be end-capped with a variety of reaction-based detection units. Upon application of the appropriate stimulus and exposure to basic conditions, the poly(benzyl ethers) undergo an anionic elimination cascade to release their constituent monomers within minutes. While some current examples of depolymerizable polymers show significant levels of background degradation, these poly(benzyl ethers) remain stable against non-selective degradation from acid, base, or heat while end-capped. Furthermore, a current challenge with depolymerizable polymers is creating polymers that respond in the solid state, due to the low polarity environment within the polymer matrix and conformational restriction of the polymer chains. We have addressed this issue by creating functionalized monomers with pendant reaction-based detection units. These modified units allow for increased interaction with the solution phase, enabling depolymerization of the solid state polymer. This presentation will focus on these results, as well as current efforts that are aimed at making derivatives of the poly(benzyl ethers) with diverse physical and chemical properties to be used as stimuli responsive materials.

Synthesis and selective depolymerization of poly(benzyl ethers) for stimuli responsive materials

248th National Meeting (2014)

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