Application of phenolic radicals for antioxidants, as active materials in batteries, magnetic materials and ligands for metal-complexes

Jähnert, Thomas; Hager, Martin D.; Schubert, Ulrich S.

doi:10.1039/c4ta03023k

Cited by 58 publications

(31 citation statements)

References 171 publications

(258 reference statements)

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“…A wide range of redox potentials and theoretical capacities are accessible via different chemistries (See Table S2, shown in Figure 3a) [92,99,[137][138][139][140]. The theoretical capacity is defined as F a/F w where F is the Faraday constant, a is the number of charges that can be stored on a particular monomer, and F w is the formula weight of the monomer.…”

Section: Electrochemical Propertiesmentioning

confidence: 99%

Engineering radical polymer electrodes for electrochemical energy storage

Nevers

Brushett

Wheeler

2017

Journal of Power Sources

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In principle a wide range of organic materials can store energy in the form of reversible redox conversions of stable radicals. Such chemistry holds great promise for energy storage applications due to high theoretical capacities, high rate capabilities, intrinsic structural tunability, and the possibility of low-cost "green" syntheses from renewable sources. There have been steady improvements in the design of organic radical polymers, in which radicals are incorporated into the backbone and/or as pendant groups. This review highlights opportunities for improved redox molecule and polymer design along with the key challenges (e.g., transport phenomena, solubility, and reaction mechanisms) to transitioning known organic radicals into high-performance electrodes. Ultimately, organic-based batteries are still a nascent field with many open questions. Further advances in molecular design, electrode engineering, and device architecture will be required for these systems to reach their full potential and meet the diverse and increasing demands for energy storage.

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Section: Electrochemical Propertiesmentioning

confidence: 99%

Engineering radical polymer electrodes for electrochemical energy storage

Nevers

Brushett

Wheeler

2017

Journal of Power Sources

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“…[23] Angewandte Chemie Zuschriften Them ulti-step reversible electrochromic properties of 1C are noteworthy,g iven that the galvinoxyl radical shows only aone-step reversible redox process at À0.06 V(vs.Ag/AgCl) that corresponds to one-electron reduction under similar conditions. [22] This comparison clearly demonstrates the impact of the p extension in 1C with the cycloheptadithiophene skeleton. More importantly,t he thus resulting cation 1 + is different from 1H + ,w hich is generated in situ upon protonation.…”

mentioning

confidence: 85%

A Near‐Infrared Dye That Undergoes Multiple Interconversions through Acid–Base Equilibrium and Reversible Redox Processes

2017

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An ear-infrared (NIR) polymethine dye (1), consisting of ac yclohepta [1,2-b;4,3-b']dithiophene and two phenol moieties,w as synthesized. This dye exhibited pHresponsive changes in its photophysical properties due to atwostep acid-base equilibrium that produced ap rotonated cation (1H + )a nd an anion (1 À ). While 1H + showed an intense fluorescence in the red region of the visible spectrum, 1 À exhibited astrong absorption in the NIR region. The tropylium ion character in 1H + induces high pK a1 and pK a2 values for 1. Moreover,astable radical (1C)w as prepared, whichs howed aNIR absorption band with amaximum at circa 1600 nm. The cyclic voltammogram of 1C revealed atwo-step reversible redox process that produced 1 À and the cation 1 + ,which is different from 1H + .T hese redoxp rocesses accompany drastic electrochromic changes in the vis-NIR region. Overall, 1 is susceptible to multiple interconversions between five forms,due to the multifaceted character of the cycloheptadithiophene skeleton.

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“…Organic radical polymers have received significant attention over the last two decades because of their redox‐active nature and found wide‐ranging application in a variety of fields including catalysis, spin probes, imaging agents, antibiofilm coatings, and most prominently of all, as electroactive materials in organic radical batteries (ORB) . The current trend towards renewable energy and increased environmental awareness has boosted research into organic‐based materials for energy applications promising safer, more powerful and environmentally friendly technologies .…”

Section: Introductionmentioning

confidence: 99%

A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach

et al. 2020

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An alternative synthetic route towards the widely employed electroactive poly(TEMPO methacrylate) (PTMA) via a thermally robust methoxyamine‐protecting group is demonstrated herein. Protection of the radical moiety of hydroxy‐TEMPO with a methyl functionality and subsequent esterification with methacrylic anhydride allows the high‐yielding formation of the novel monomer methyl‐TEMPO methacrylate (MTMA). The polymerization of MTMA to poly(MTMA) (PMTMA) is investigated via free radical polymerization and reversible addition–fragmentation chain‐transfer polymerization (RAFT), a reversible‐deactivation radical polymerization technique. Cleavage of the temperature‐stable methoxyamine functionality by oxidative treatment of PMTMA with meta‐chloroperbenzoic acid (mCPBA) releases the electroactive PTMA. The redox activity of PTMA was confirmed by cyclic voltammetry in lithium‐ion coin cells.

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Application of phenolic radicals for antioxidants, as active materials in batteries, magnetic materials and ligands for metal-complexes

Cited by 58 publications

References 171 publications

Engineering radical polymer electrodes for electrochemical energy storage

Engineering radical polymer electrodes for electrochemical energy storage

A Near‐Infrared Dye That Undergoes Multiple Interconversions through Acid–Base Equilibrium and Reversible Redox Processes

A Methoxyamine‐Protecting Group for Organic Radical Battery Materials—An Alternative Approach

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