Conjugated electrochromic polymers with amide-containing side chains enabling aqueous electrolyte compatibility

Perera, Kuluni; Yi, Zhengran; You, Lijun; Ke, Zhifan; Mei, Jianguo

doi:10.1039/c9py01066a

Cited by 24 publications

(29 citation statements)

References 30 publications

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“…In a chloroform solution, all the polymers exhibited a maximum absorption at around 537 nm with a shoulder peak absorption at ~575 nm, similar to the absorption spectrum of PProDOT-(CH 2 OEtHx) 2 consisting purely of alkyl sidechains (Figure S14b). 60,63 This result is consistent with previous reports of polythiophene-based CRPs, [28][29][30] indicating minimum influence of the TEMPO side chain on the electronic structure of the PProDOT backbone in the solution state. While the TEMPObearing monomer units (i.e., M1 and M1-Br 2 ) appear orange in solution, with an absorption peak at 458 nm that is associated with the nitroxide radical functionality (Figure S14a), 18,22 this peak cannot be distinguished in the UV-Vis absorption spectra of the radical polymers, due to the overlap with the absorption bands of the PProDOT backbone and the significantly lower molar absorptivity of the TEMPO unit relative to the thiophenebased backbone.…”

Section: Resultssupporting

confidence: 91%

Impact of open‐shell loading on mass transport and doping in conjugated radical polymers

Liu

Perera

Wang

et al. 2021

Journal of Polymer Science

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Radical-containing polymers are an evolving class of redox-active macromolecules that have received great interest; however, most reports regarding radical polymers have focused on materials with nonconjugated backbones because their application drivers did not require this conjugation. Conversely, there has been a recent rise in the development of radical polymers for nextgeneration applications where imparting conjugation to the backbone of the radical polymer could be of significant benefit. To this end, we designed and synthesized a series of 3,4-propylenedioxythiophene (ProDOT)-based polymers bearing nitroxide radical pendent groups via direct arylation polymerization. Specifically, we present four radical polymers with open-shell loadings ranging from 24% to 82% of the total number of repeat units per polymer chain. The impact of openshell loading on the electrochemical behaviors of these polymers in different electrolytes was then established using cyclic voltammetry, spectroelectrochemical analyses, and electrochemical quartz-crystal microbalance with dissipation monitoring. We demonstrate that incorporating the open-shell moieties in the ProDOT-based polymers lowers the oxidation onset potential of the conjugated backbone and increases the solvent and ion uptake significantly. Thus, this effort provides a clear picture of the mass transfer and doping mechanism of the ProDOT-based radical polymers to aid in guiding their future design.

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Section: Resultssupporting

confidence: 91%

Impact of open‐shell loading on mass transport and doping in conjugated radical polymers

Liu

Perera

Wang

et al. 2021

Journal of Polymer Science

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“…[114] Recently, Perera et al investigated the electrochromic modified polymers based on poly(3,4-propylenedioxythiophene) (PProDOT) with their promising redox properties used for enhanced optical contrast. [115] Xu et al synthesized novel indole[3,2-b]carbazolebased electrochromic polymers with outstanding photonic contrast, fast switching rate, and satisfactory cycling stability. [116] Despite the fact that two latter works are devoted to the modification of thin films, we see the potential to further implement these methods for nanoparticulate adaptive complexes.…”

Section: Electrically Responsive Complexesmentioning

confidence: 99%

“…[122] Magnetic response generated from Fe 3 O 4 NPs depends on their size, shape, size distribution, and other parameters (Figure 11A). [114][115][116] To obtain the dynamic magnetic NP-polymer complexes, the NPs can be functionalized with stimuli-responsive polymers. These core-shell particles can be further loaded with drugs and applied as drug delivery platforms.…”

Section: Magnetic-responsive Complexesmentioning

confidence: 99%

“…investigated the electrochromic modified polymers based on poly(3,4‐propylenedioxythiophene) (PProDOT) with their promising redox properties used for enhanced optical contrast. [ 115 ] Xu et al. synthesized novel indole[3,2‐b]carbazole‐based electrochromic polymers with outstanding photonic contrast, fast switching rate, and satisfactory cycling stability.…”

Section: Adaptive Np‐polymer Complexesmentioning

confidence: 99%

“…[ 122 ] Magnetic response generated from Fe 3 O 4 NPs depends on their size, shape, size distribution, and other parameters ( Figure A). [ 114–116 ]…”

Section: Adaptive Np‐polymer Complexesmentioning

confidence: 99%

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Adaptive Nanoparticle‐Polymer Complexes as Optical Elements: Design and Application in Nanophotonics and Nanomedicine

Talianov

Fatkhutdinova

Timin

et al. 2021

Laser & Photonics Reviews

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Over the last few decades, nanomaterials have attracted significant attention in diverse applications. Today, a new generation of nanomaterials, which demonstrate tunable physical and chemical properties, is able to address modern challenges in personalized medicine, adaptive optics and smart chemistry. Here, a special class of such nanomaterials -biointegrated nanoparticle-polymer complexes and their ensembles with tunable optical properties are reviewed. Key aspects of the design and synthesis of such complexes exhibiting dynamic structural changes to different external and internal stimuli (e.g., light, chemical, temperature, electric/magnetic fields and others) are discussed. Consequently, these changes allow one to tune the optical response in reversible or irreversible manner. The application of such complexes is considered as functional adaptive elements for optical filters, sensors, Bragg mirrors, artificial muscles, and drug delivery. The current state and the perspectives of further development of this research area are discussed.

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Branched Oligo(ether) Side Chains: A Path to Enhanced Processability and Elevated Conductivity for Polymeric Semiconductors

Jones

Keersmaecker

Savagian

et al. 2021

Adv Funct Materials

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conjugated polymers (CPs) with tunable electronic properties will remain a challenge without adequate solution processability due to the importance of techniques such as roll-to-roll manufacturing. Consequently, modifying CP backbones with polar side chains has recently resurged as an attractive structural design approach to improve polymer solubility and to provide CPs with the capability of transporting both electrons and ions, which is crucial for applications such as organic electrochemical transistors (OECTs). Here, a new dioxythiophene copolymer comprised of 2, 2'-bis-(3,4-ethylenedioxy)thiophene (biEDOT) and 3,4-propylenedioxythiophene (ProDOT) substituted with branched oligo(ether) side chains (PE 2 -biOE2OE3) is synthesized using two direct hereto(arylation) polymerization (DHAP) techniques. The typical DHAP technique results in a lower molecular weight polymer (PE 2 -biOE2OE3(L)), which is soluble in acetone and demonstrated a solid-state conductivity after oxidative doping of 55 ± 3 S cm −1 . Alternatively, a unique temperature ramp DHAP methodology results in a higher molecular weight polymer (PE 2 -biOE2OE3(H)) with an especially high solidstate conductivity of 430 ± 60 S cm −1 . Notably, the first OECT fabricated from an acetone-processed polymer is reported, which is stable up to 500 cycles and can provide a pathway for future material design aimed at eliminating the use of toxic chlorinated solvents in OECT active layer processing.

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Conjugated electrochromic polymers with amide-containing side chains enabling aqueous electrolyte compatibility

Abstract: This work illustrates an effective side-chain modification approach using amide functional groups to induce aqueous electroactivity to ProDOT-based electrochromic polymers.

Cited by 24 publications

References 30 publications

Impact of open‐shell loading on mass transport and doping in conjugated radical polymers

Impact of open‐shell loading on mass transport and doping in conjugated radical polymers

Adaptive Nanoparticle‐Polymer Complexes as Optical Elements: Design and Application in Nanophotonics and Nanomedicine

Branched Oligo(ether) Side Chains: A Path to Enhanced Processability and Elevated Conductivity for Polymeric Semiconductors

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