Poly(methacrylates) with Pendant Benzoquinone Units – Monomer Synthesis, Polymerization, and Electrochemical Behavior: Potential New Polymer Systems for Organic Batteries

Abstract

Redox-active polymers became the focus of attention in the fi eld of organic electronics during the last decade. Quinoide systems are intensively studied in this fi eld. Although benzoquinones are generally known as radical scavengers, certain monomers can be polymerized by radical polymerization techniques. For this purpose, methacrylate functionalities are attached to the redox-active quinone moiety. A free-radical polymerization technique is applied utilizing AIBN as initiator. The molar mass can be adjusted by the choice of an appropriate solvent system. Electrochemical investigations of these new monomers and polymers, in particular cyclic voltammetry, are performed in aqueous and non-aqueous electrolytes in the dissolved and solid states, showing the potential usefulness of the system for applications in organic radical batteries.

Cytosolic NQO1 Enzyme-Activated Near-Infrared Fluorescence Imaging and Photodynamic Therapy with Polymeric Vesicles

“…NQO1-responsive amphiphilic BCPs were synthesized by combining controlled free radical polymerization (CRP) and postmodification. It is wellknown that quinone moieties could retard free radical polymerization, 70 thus quinone-containing monomers could not be directly polymerized by CRP techniques such as reversible addition−fragmentation chain transfer (RAFT) polymerization. We chose to synthesize BCPs containing highly reactive isocyanate functionalities via RAFT polymerization, followed by postmodification with hydroxyl-containing quinone derivatives, by taking advantage of high-efficiency isocyanate-hydroxyl addition reaction under catalyzed conditions (Schemes S1 and S2).…”

Carbon allotropes grafted with poly(pyrrole) derivatives via living radical polymerizations: electrochemical analysis of nano-composites for energy storage

“…Also, the oxygen containing functionalities in polyacrylates are not stable under oxidizing potential. 40 A possible solution would be to engage the sulfur end-capped chains, as it was done for e-ATRP. Overall, this chemical modication makes e-ATRP composites still relatively stable, as indicated by multiple chronopotentiometric scans ( Fig.…”

Crystal structures of the polymer precursors 3-(2,5-dimethoxy-3,4,6-trimethylphenyl)propyl methacrylate and 3-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)propyl methacrylate

“…Redox-active polymers containing 2,2,6,6tetramethylpiperidin-1-oxyl-4-yl (TEMPO) and ferrocene as pendant groups are well documented (Gracia & Mecerreyes, 2013;Tamura et al, 2008;Schattling et al, 2014). In contrast, polymers with pendant quinone units are less well explored (Hodge & Gautrot, 2009;Hä upler et al, 2014). Reasons for this include their free-radical-scavenging properties in free radical polymerization (FRP), and the incompatibility of the quinone carbonyl groups in typical living polymerization such as anionic or cationic polymerization.…”