Recent advances in the synthesis and structure–property relationships of ammonium ionenes

Williams, Sharlene R.; Long, Timothy Edward

doi:10.1016/j.progpolymsci.2009.04.004

Cited by 124 publications

(69 citation statements)

References 86 publications

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“…[ 30 ] Decreases in the onset of weight loss with varying alkyl substituents suggested a degradation process similar to a Hofmann elimination for ammonium-containing species. [ 31 ] However, a twostep degradation did not occur for the imidazolium homopolymers suggesting rapid backbone degradation following onset of weight loss. As expected, counteranion selection also infl uenced the T g 's of the polyelectrolytes (Figure 2 ).…”

Section: Methodsmentioning

confidence: 99%

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Green

Cruz

et al. 2011

Macro Chemistry & Physics

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Structure-property relationships for polymerized ionic liquids (PILs) relate chemical structure to ionic conductivity and reveal the importance of glass transition temperature ( T g ) and the energy associated with an ion-hopping mechanism for ion conduction for a series of alkyl-substituted vinylimidazolium PILs. The alkyl-substituted vinylimidazolium-based PILs with varying lengths of n -alkyl substituents provide diverse precursors with exchangeable anions to further enhance thermal stability and ionic conductivity. As the anion size increases, regardless of alkyl substituent length, T g decreases and the onset of weight loss, T D , increases. As the length of the alkyl substituent increases, T g decreases for PILs with Br − and BF 4 − counteranions. Ionic conductivity increases over an order of magnitude upon exchange of the counteranion from TfO − < Tf 2 N − . due to their unique combination of physical properties including high thermal stability, wide electrochemical window, negligible vapor pressure, and potentially high ionic conductivities. [3][4][5][6][7] Two particular classes of ILs are polymerizable ILs (PILs) that contain polymerizable functional groups and room temperature ILs (RTILs) with melting temperatures at or below room temperature. [ 8 ] Potential applications have included electrolytes in electromechanical transducers, artifi cial muscle fabrication, and non-volatile solvents for a myriad of chemical reactions. [ 9 ] Chen and Elabd investigated the solution properties and subsequent formation of electrospun fi bers of an imidazolium-containing methacrylate-based PIL. [ 10 ] This study revealed solution properties similar to polyelectrolyte solutions, and electrospun fi bers formed with intermediate fi ber diameters and onset of fi ber formation between polyelectrolyte and neutral polymers. The fi brous mats exhibited promising ionic conductivities at room temperature, and upon swelling with a RTIL, ionic conductivities were on the order of 10 mS cm − 1 . Long and co-workers also investigated the impact of counteranion on the solution and thermal properties of ammoniumbased polyelectrolytes. [ 11 ] Our study revealed the important infl uence of anion selection on the T g of the polyelectrolyte, and we observed polyelectrolyte electrospinning

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Section: Methodsmentioning

confidence: 99%

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Green

Cruz

et al. 2011

Macro Chemistry & Physics

Self Cite

146

189

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“…31,31 Cationic PILs can be synthesized by polymerization of IL monomers (ILMs), by polymerization of complementary neutral quaternizable monomers (i.e. for the synthesis of ionenes, 32 ) or by postpolymerization introduction of charged species by either alkylation reactions or by ligation of functional ILs. All these strategies rely at some point either on chain growth or on step growth polymerization mechanisms and eventually a subsequent anion exchange reaction.…”

Section: Structure and Preparation Of Cationic Poly(ionic Liquid)smentioning

confidence: 99%

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

2016

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Poly(ionic liquid)s (PILs) are a unique class of polyelectrolytes having properties suited for modern technological applications such as electrochemical devices (batteries, supercapacitors, light-emitting electrochemical cells), ion-gated field effect transistors, electrochromic devices, fuel cells, dye sensitized solar cells, catalysis, or soft robotics. Their structure and properties can be finely tuned by unlimited combinations issued from extended pools of cationic and anionic building blocks. In a constant quest for the development of solid polymer electrolytes with enhanced physical, mechanical and (electro)chemical properties, a new class of PILs based on 1,2,3-triazolium cations has been recently developed. Their preparation takes advantage of the beneficial features of the multiple combinations between the Click chemistry philosophy with macromolecular engineering techniques to afford tunable and highly functional ion conducting materials thus stretching out the actual boundaries of PILs macromolecular design. This feature article summarizes the different strategies developed so far for the synthesis of 1,2,3-triazolium-based PILs (TPILs) since their first introduction in 2013.

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“…The rapid progress and explosive development in this field is reflected by the very large body of recent publications. [9][10][11][12] The major advantages of using a PIL instead of an IL are the enhanced mechanical stability, improved processability, durability, and spatial controllability over the IL species via macromolecular architecture. Their promising applications involve polymeric electrolytes, catalytic membranes, ionic conductive materials, carbon dioxide absorbents, microwave absorbing materials, stabilizing agent, and carbon precursors.…”

Section: Introductionmentioning

confidence: 99%

Poly(ionic liquid) Latexes Prepared by Dispersion Polymerization of Ionic Liquid Monomers

2011

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In this contribution, we report the facile preparation of vinylimidazolium-typed poly(ionic liquid) (PIL) latexes and nanoparticles via dispersion polymerization of ionic liquid monomers in aqueous solutions. A homologous series of vinylimidazolium-typed ionic liquid monomers with different alkyl tail length (C8-C18) were synthesized via quaternization of 1-vinylimidazole with corresponding n-alkyl bromides. Dispersion polymerization of these monomers was conducted at a monomer concentration of 50 g/L in aqueous solution at 70°C without addition of further stabilizers. For ionic liquid monomers with sufficiently long alkyl chains (gC12), PILs nanoparticles of 20-40 nm in diameter were found, which were self-stabilizing in aqueous media. In the same procedure, preparation of cross-linked PIL nanoparticles was performed in the presence of 10 mol % of divinylimidazolium-based cross-linker. The as-synthesized crosslinked PIL nanoparticles could be transferred into organic solvents, such as polar DMF, and nonpolar toluene after anion exchange with lithium bis(trifluoromethylsulfonyl)imide. This dispersion polymerization requires no dispersing agent and potentially enables a large scale synthesis of PIL nanoparticles in both aqueous and organic solutions. The application spectrum of this unique type of organic nanoparticles is expectedly broad; e.g., the particles are useful as powerful binders and dispersants for coatings and as colloidal templates.

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Recent advances in the synthesis and structure–property relationships of ammonium ionenes

Cited by 124 publications

References 86 publications

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Alkyl‐Substituted N‐Vinylimidazolium Polymerized Ionic Liquids: Thermal Properties and Ionic Conductivities

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

Poly(ionic liquid) Latexes Prepared by Dispersion Polymerization of Ionic Liquid Monomers

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