Effects of electronics, aromaticity, and solvent polarity on the rate of azaquinone-methide-mediated depolymerization of aromatic carbamate oligomers

Jessica S. Robbins, Kyle M. Schmid, Scott T. Phillips

Research output: Contribution to journalArticle

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Abstract

This paper uses physical-organic studies on well-defined oligomers to establish design principles for creating aromatic poly(carbamates) that depolymerize from head-to-tail in low dielectric constant environments when exposed to specific applied signals. We show that either increasing electron density or decreasing the aromaticity of aromatic repeating units in poly(carbamates) increase the overall depolymerization rate. For example, a methoxybenzene-based repeating unit provides depolymerization rates that are 143× faster than oligomers that contain a benzene-based repeating unit. Furthermore, the rate of depolymerization in the methoxybenzene-based system is tolerant to low dielectric environments, whereas the benzene-based oligomers are not.

Original languageEnglish (US)
Pages (from-to)3159-3169
Number of pages11
JournalJournal of Organic Chemistry
Volume78
Issue number7
DOIs
StatePublished - Apr 5 2013

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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