The multicomponent Debus–Radziszewski reaction in macromolecular chemistry

Saxer, Samantha; Marestin, Catherine; Merçier, Régis; Dupuy, Jérôme

doi:10.1039/c8py00173a

Cited by 57 publications

(45 citation statements)

References 69 publications

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“…Imidazoles are also typically more convenient to work and more synthetically versatile than amines, pyridines, and especially phosphines . Furthermore, in addition to the Menshutkin reaction, modified Debus–Radziszewski reactions can also be employed to form imidazolium‐based ionenes . Yet, despite these promising characteristics, there has been scant fundamental or applied studies with even simple imidazolium ionenes and what knowledge exists is relatively disparate compared to ammonium ionenes.…”

Section: Imidazolium Ionenesmentioning

confidence: 99%

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers

Bara

O’Harra

2019

Macro Chemistry & Physics

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Ionenes, condensation polymers wherein the charge (typically cationic) lies directly within the polymer backbone, have been known for over 85 years. Historically, ionenes have been synthesized from 3o diamines and α,ω‐dihaloalkanes, forming chains of ammonium cations tethered by flexible hydrocarbon linkages with “free” halide anions. However, the requisite building blocks of ionenes are by no means limited only to such molecules. In recent years, ionenes with more sophisticated backbone chemistries have been produced, with a trend toward the use of functionalities associated with classical “high‐performance” condensation polymers such as polyimides and polyarylamides. The expansion of ionenes is also catalyzed by the rapid growth of research in imidazolium‐based ionic liquids (ILs), wherein the combination of ionenes with ILs can yield unexpected behaviors. Furthermore, when considering the largely unexplored experimental space in anionic ionenes, the opportunities for new materials are virtually endless. This review primarily focuses on developments in ionenes published in the scientific literature since 2010, but also includes some older examples that may not have received sufficient attention at the time of their original publication yet can provide some key lessons for the future of ionene design.

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Section: Imidazolium Ionenesmentioning

confidence: 99%

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers

Bara

O’Harra

2019

Macro Chemistry & Physics

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“…Examples include click and click-inspired reactions and multicomponent reactions. [61][62][63][64][65][66][67][68][69][70][71][72][73][74] Thus, this first polymeric probe for the detection of FA in biological systems via the Hantzsch reaction might prompt a broad, in-depth study of organic reactions in polymer science for discovering several new functional polymers with interesting properties for applications in biological and medical areas.…”

Section: Discussionmentioning

confidence: 99%

Polymers for Fluorescence Imaging of Formaldehyde in Living Systems via the Hantzsch Reaction

et al. 2018

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“…The D–R reaction, a simple and efficient three‐multicomponent reaction, was proposed 100 years ago by Debus and Radziszewski, that involves an 1.2‐dicarbonyl compounds, an ammonia, and an aldehyde to yield imidazole derivatives in a water medium. [ 177–179 ] This reaction overcomes the difficulty of preparing imidazole ionic liquids by traditional grafting method, which is time‐consuming and has low yield. [ 180 ] In addition, the D–R reaction is the first controlled MCR to form a polymer chain under mild reaction conditions, and the synthetic imidazole cation is regularly attached to the main chain of polymer instead of the side chain.…”

Section: Fabrication Of Polymeric Composites Based On Mcrs For Removamentioning

confidence: 99%

Recent Advances on Fabrication of Polymeric Composites Based on Multicomponent Reactions for Bioimaging and Environmental Pollutant Removal

Yang

Liang

et al. 2021

Macromol. Rapid Commun.

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As the core of polymer chemistry, manufacture of functional polymers is one of research hotspots over the past several decades. Various polymers are developed for diverse applications due to their tunable structures and unique properties. However, traditional step‐by‐step preparation strategies inevitably involve some problems, such as separation, purification, and time‐consuming. The multicomponent reactions (MCRs) are emerging as environmentally benign synthetic strategies to construct multifunctional polymers or composites with pendant groups and designed structures because of their features, such as efficient, fast, green, and atom economy. This mini review summarizes the latest advances about fabrication of multifunctional fluorescent polymers or adsorptive polymeric composites through different MCRs, including Kabachnik–Fields reaction, Biginelli reaction, mercaptoacetic acid locking imine reaction, Debus–Radziszewski reaction, and Mannich reaction. The potential applications of these polymeric composites in biomedical and environmental remediation are also highlighted. It is expected that this mini‐review will promote the development preparation and applications of functional polymers through MCRs.

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The multicomponent Debus–Radziszewski reaction in macromolecular chemistry

Cited by 57 publications

References 69 publications

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers

Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers

Polymers for Fluorescence Imaging of Formaldehyde in Living Systems via the Hantzsch Reaction

Recent Advances on Fabrication of Polymeric Composites Based on Multicomponent Reactions for Bioimaging and Environmental Pollutant Removal

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