Increasing the Rate of End-to-end Depolymerization of Poly(benzyl carbamates) in Low Polarity Environments

Open Access
Author:
Robbins, Jessica Sloane
Graduate Program:
Chemistry
Degree:
Doctor of Philosophy
Document Type:
Dissertation
Date of Defense:
June 04, 2014
Committee Members:
  • Scott T Phillips, Dissertation Advisor
  • Scott T Phillips, Committee Chair
  • Alexander Thomas Radosevich, Committee Member
  • Ayusman Sen, Committee Member
  • Michael Anthony Hickner, Special Member
Keywords:
  • stimuli-responsive materials
  • depolymerization
  • polymer synthesis
  • point-of-care diagnostics
  • paper-based microfluidic devices
Abstract:
The design and synthesis of stimuli-responsive polymers that undergo end-to-end depolymerization in response to specific chemical or physical signals have become an increasingly important challenges in polymer chemistry. Depolymerizable polymers have been used in a variety of applications including as signal amplification reagents for sensors, responsive capsules, shape-shifting plastics, and autonomous analyte-responsive pumps. Poly(benzyl carbamates), one of the major classes of depolymerizable polymers, depolymerize via a series of azaquinone methide elimination reactions down the polymer backbone. The formation of azaquinone methide is slow (i.e., hours or days) in low-polarity environments (e.g., solutions with dielectric constants lower than that of water, or solid-state polymeric materials), which limits the utility of poly(benzyl carbamates) in applications that require low-polarity environments. This Thesis describes efforts to design derivatives of poly(benzyl carbamates) that depolymerize rapidly from end-to-end in response to specific signals in environments less polar than water, and the application of these new derivatives as phase-switching reagents in assays performed in paper-based microfluidic devices.