From monomer synthesis to polymers with pendant aldehyde groups

Négrell, Claire; Voirin, Coline; Boutevin, Bernard; Ladmiral, Vincent; Caillol, Sylvain

doi:10.1016/j.eurpolymj.2018.10.039

Cited by 16 publications

(16 citation statements)

References 204 publications

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“…FTIR spectra of pristine GCF and PEIAA-GCF samples reveal that the PEIAA-GCF sample had amino and carboxylic acid groups (amines and carboxylic acids). In the case of the pristine GCF, Figure 2 shows oxygen-containing groups in the PEIAA-GCF over a very broad band in the 3300-2500 cm -1 region for hydroxyl (O-H) stretching, 3 Energy Material Advances intense bands from 1760 to 1690 cm -1 and 1320-1200 cm -1 corresponding to C=O (polymeric aldehyde segment with carboxylic acids) [24,25]. C-OH vibration comprised of a mixture of C-O stretch and C-O-H bend with the appearance of typical N-H and C-N stretching vibrations corresponding to amine groups and PEI backbone.…”

Section: Resultsmentioning

confidence: 99%

Crosslinked Polyethyleneimine Gel Polymer Interface to Improve Cycling Stability of RFBs

et al. 2022

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Redox flow batteries are considered a promising technology for grid energy storage. However, capacity decay caused by crossover of active materials is a universal challenge for many flow battery systems, which are based on various chemistries. In this paper, using the vanadium redox flow battery as an example, we demonstrate a new gel polymer interface (GPI) consisting of crosslinked polyethyleneimine with a large amount of amino and carboxylic acid groups introduced between the positive electrode and the membrane. The GPI functions as a key component to prevent vanadium ions from crossing the membrane, thus supporting stable long-term cycling. Cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) measurements were conducted to investigate the effect of GPI on the electrochemical properties of graphitic carbon electrodes (GCFs) and redox reaction of catholyte. X-ray photoelectron spectroscopy (XPS) and 1H nuclear magnetic resonance (NMR) spectra demonstrated that the crosslinked GPI is chemically stable for 100 cycles without dissolution of polymers and swelling in the strong acidic electrolytes. Results from inductively coupled plasma mass spectrometry (ICP-MS), Fourier-transform infrared (FTIR) spectroscopy, and energy-dispersive X-ray (EDX) spectroscopy proved that the GPI is effective in maintaining the concentration of vanadium species in their respective half-cells, resulting in improved cycling stability because of it prevents active species from crossing the membrane and stabilizes the oxidation states of active species.

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Section: Resultsmentioning

confidence: 99%

Crosslinked Polyethyleneimine Gel Polymer Interface to Improve Cycling Stability of RFBs

et al. 2022

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“…Aldehyde groups are widely used in various applications such as food additives and agrochemistry, as well as the textile and leather industries and in polymer studies . The aldehyde unit, even incorporated in various polymers, can be easily converted to many other functionalities . Importantly, polymers bearing aldehyde functionalities are highly attractive because they demonstrate greatly reduced toxicity versus molecular aldehydes …”

Section: Results and Discussionmentioning

confidence: 99%

Palladium-Catalyzed Dimerization of Vinyl Ethers: Mechanism, Catalyst Optimization, and Polymerization Applications

2019

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The electron-rich nature of vinyl ethers (CH 2  CHOR) enables their versatile reactivity patterns with transition metal catalysts. Furthermore, they are highly attractive monomers for the synthesis of many polymers and copolymers. However, it is challenging to incorporate these substrates in transition metalcatalyzed olefin polymerization due to various side reactions such as cationic polymerization and β-OR elimination. The Brookharttype α-diimine palladium system can lead to the formation of branched (co)polymers with unique microstructures and potentially unique properties due to the characteristic chain-walking mechanism. Unfortunately, common vinyl ethers will induce cationic polymerization and catalyst decomposition for these catalysts. Within this context, the generation of ether-functionalized polyolefins with branched microstructures is attractive but remains a great challenge. In this study, we developed a system that combines palladium-catalyzed dimerization of vinyl ethers for the generation of β,γ-unsaturated acetals and palladium-catalyzed ethylene copolymerization with a dimerization product for the generation of polar functionalized branched polyolefins. The mechanism and catalyst optimization for the dimerization reaction were investigated in detail. This strategy combines catalytic organic synthesis and transition metal-mediated ethylene copolymerization to incorporate the abundant but challenging vinyl ether substrates into polyolefins. Importantly, the inserted acetal moiety can be readily converted to various functional groups through postpolymerization functionalization reactions, making this strategy even more versatile.

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“…Furthermore, this method also allows the conjugation of biomacromolecules such as proteins. An additional advantage of this functionalization strategy is that the many aldehyde containing monomers tolerate radical polymerization processes . Moreover, the introduction of a new functionality does not come along with the introduction of a large passive linker.…”

Section: Other Reactions For Particle Functionalizationmentioning

confidence: 99%

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

Gruber

Navarro

Klinger

2019

Adv Materials Inter

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Precise control of the chemical functionality of polymer nanoparticles is a key requirement in tailoring their (dynamic) colloidal properties toward advanced applications. However, current synthetic techniques are still limited in the versatility of chemical design and preparation of such functional colloidal nanomaterials. Two major challenges remain: First, various particle preparation methods are restricted in their functional group tolerance, thus hindering certain combinations of polymer backbones with specific functional groups. Second, the preparation of particles with different functionalities requires the synthesis of different particle batches. But this often results in a simultaneous variation of colloidal features. As a result, the accurate determination of important structure–property relations is still hindered. To address these restrictions, postmodification of preformed reactive particles is gaining more attention. This technique has evolved from polymer synthesis, where postpolymerization functionalization enables the introduction of a plethora of functional groups without changing the degree of polymerization and the molecular weight distribution. Similarly, modifying precursor particles enables the introduction of functional groups into particles while reducing variations in colloidal features, e.g., particle size and size distribution. This powerful synthetic method complements established procedures for functionalization of particle surfaces, thereby enabling the facile preparation of (multi‐)functional particle libraries, which will allow precise investigations of structure–property relations.

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From monomer synthesis to polymers with pendant aldehyde groups

Cited by 16 publications

References 204 publications

Crosslinked Polyethyleneimine Gel Polymer Interface to Improve Cycling Stability of RFBs

Crosslinked Polyethyleneimine Gel Polymer Interface to Improve Cycling Stability of RFBs

Palladium-Catalyzed Dimerization of Vinyl Ethers: Mechanism, Catalyst Optimization, and Polymerization Applications

Reactive Precursor Particles as Synthetic Platform for the Generation of Functional Nanoparticles, Nanogels, and Microgels

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