Post-polymerization modification and organocatalysis using reactive statistical poly(ionic liquid)-based copolymers

Coupillaud, Paul; Vignolle, Joan; Mecerreyes, David; Taton, Daniel

doi:10.1016/j.polymer.2014.02.043

Cited by 40 publications

(49 citation statements)

References 67 publications

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“…The most popular route to obtain Ag(I)‐NHC compounds uses Ag 2 O, allowing the direct conversion of imidazolium salts (ionic liquids; ILs) into the corresponding metal complexes by transmetalation reaction. Thus, in comparison to the approaches used to produce Zn‐ and Sn‐NHC complexes, the free carbenes do not interfere with the synthesis of Ag(I)‐NHC, allowing to achieve good yields using standard laboratory techniques …”

Section: Methodsmentioning

confidence: 99%

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Garmendia

Lawrenson

Arno

et al. 2019

Macromol. Rapid Commun.

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The need for efficient, tailor‐made catalysts has inspired chemists to design synthetic macromolecular architectures for selective catalysis. To this purpose, herein the synthesis and in‐depth characterization of Ag(I)‐crosslinked single‐chain nanoparticles (SCNPs) is reported and their application as catalysts is demonstrated. Specifically, a copolymer of styrenic benzimidazolium chloride is synthesized as a linear precursor via reversible addition‐fragmentation chain‐transfer polymerization. Metalation of the benzimidazolium moieties by Ag(I) resulted in the intramolecular cross‐linking of single chains via the formation of silver‐N‐heterocyclic carbene (Ag‐NHC) linkages under dilute conditions. The successful formation of well‐defined, robust SCNPs is evidenced by size‐exclusion chromatography, dynamic light scattering, nuclear magnetic resonance spectroscopy, and transmission electron microscopy. Finally, it is demonstrated that the Ag‐SCNPs can be used as NHC pre‐catalysts, by first indirectly evidencing the formation of the corresponding unfolded NHC‐CS2 polybetaine and then organocatalysing a benzoin condensation reaction.

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Section: Methodsmentioning

confidence: 99%

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Garmendia

Lawrenson

Arno

et al. 2019

Macromol. Rapid Commun.

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“…21 Recently, Bazan and co-workers utilized fullerenes such as C 60 or C 70 as the carbon-based LA to generate the thermally stable zwitterionic NHC/fullerene LB → LA adduct. 22 Inspired by this work, we reasoned that this convenient approach could offer a powerful strategy to not only synthesize high-density C 60 -containing polymers with a high level of C 60 incorporation but also provide a new route to post-modification of poly-(NHC), 23 an approach often employed to prepare recyclable versions of the versatile molecular NHC catalysts. 24 Herein we report a highly efficient and convenient approach to synthesize poly(NHC-C 60 ) with an unprecedented level of C 60 incorporation, up to 69.3 wt%, through the stable polymeric Lewis adduct formation between poly(NHC) and C 60 .…”

Section: Introductionmentioning

confidence: 99%

Polymeric carbon Lewis base–acid adducts: poly(NHC–C₆₀)

Miao

Chen

2015

Polym. Chem.

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Rapid formation of thermally robust polymeric Lewis adducts between the poly(N-heterocyclic carbene) [ poly(NHC)] Lewis base and the carbon Lewis acid C 60 is utilized to develop a powerful synthetic strategy for the convenient and efficient synthesis of C 60 -containing polymers with an unprecedented level of C 60 incorporation (up to 69.3 wt%). The resulting polymer Lewis adducts, poly(NHC-C 60 ), exhibit several intriguing properties pertaining to their molecular weights, thermal stability, cross-linking, and morphologies of donor(D)/acceptor(A) blends. Most significantly, the morphology of the D/A bulk heterojunction (BHJ) using poly(NHC-C 60 ) appears to be more controlled and the C 60 domain size is apparently much smaller and more uniform, as compared to the D/A BHJ directly using C 60 with the same D/A ratio.

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“…Apart from the conversion into functional groups, the modification of the polymer's chain can be achieved in only one reaction step, with high yield. These advantages of PPM reactions have led to many applications for PPM products, such as in catalysis, separations, surface patterning, and biomedicinal applications …”

Section: Introductionmentioning

confidence: 99%

“…Consequently, PCMSs have been usually quaternized by amines (and also pyridine) and new functional structures have been produced . Particularly, imidazolium‐based poly(ionic liquid)s can generate N ‐heterocyclic carbenes (NHCs) and poly(NHCs), for the purpose of organocatalysis …”

Section: Introductionmentioning

confidence: 99%

Imidazolium Quaternized Polymers Based On Poly(Chloromethyl Styrene) and their Complexes with FBS Proteins and DNA

Vlassi

Pispas

2015

Macromol. Chem. Phys.

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A novel series of imidazolium quaternized polymers based on poly(chloromethyl styrene) has been designed and synthesized, using nitroxide mediated polymerization and post‐polymerization functionalization. They are characterized by ATR‐FTIR (attenuated total reflectance‐Fourier transform infrared spectra) and 1H NMR in terms of functional groups and composition, which indicate the success of the synthetic scheme utilized. The solution behavior of the quaternized polymers has been investigated in water, phosphate buffer saline (PBS), and PBS(90%)‐FBS(10%) (fetal bovine serum) by static, dynamic, and electrophoretic light scattering. The functionalized polymers have been studied in terms of structure and stability during changes in temperature and ionic strength of their aqueous solutions. The copolymers form stable aggregates with positive surface charge. All cationic polymers are found to interact extensively with DNA via electrostatic interactions, forming stable complexes at certain ratios of the components.

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Post-polymerization modification and organocatalysis using reactive statistical poly(ionic liquid)-based copolymers

Cited by 40 publications

References 67 publications

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Polymeric carbon Lewis base–acid adducts: poly(NHC–C₆₀)

Imidazolium Quaternized Polymers Based On Poly(Chloromethyl Styrene) and their Complexes with FBS Proteins and DNA

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Post-polymerization modification and organocatalysis using reactive statistical poly(ionic liquid)-based copolymers

Cited by 40 publications

References 67 publications

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Catalytically Active N‐Heterocyclic Carbene Release from Single‐Chain Nanoparticles Following a Thermolysis‐Driven Unfolding Strategy

Polymeric carbon Lewis base–acid adducts: poly(NHC–C60)

Imidazolium Quaternized Polymers Based On Poly(Chloromethyl Styrene) and their Complexes with FBS Proteins and DNA

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Product

Resources

About

Polymeric carbon Lewis base–acid adducts: poly(NHC–C₆₀)