Synthesis of polymeric ionic liquids with unidirectional chain topology by AB step growth polymerization

Suckow, Marcus; Roy, Manta; Sahre, Karin; Häußler, Liane; Singha, Nikhil K.; Voit, Brigitte; Böhme, Frank

doi:10.1016/j.polymer.2017.01.063

Cited by 16 publications

(13 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Suckow et al explored the synthesis of imidazolium ionenes from “A‐B” monomers such as 1‐(6‐chlorohexyl)imidazole ( Scheme ) …”

Section: Imidazolium Ionenesmentioning

confidence: 99%

“…Such challenges were encountered by Suckow who noted that 1‐(6‐bromohexyl)imidazole was too reactive to store at ambient conditions, while 1‐(6‐chlorohexyl)imidazole was much slower to react spontaneously and as such the start of polymerization could be controlled. In order to limit the degree of polymerization to about 20 repeat units for characterization purposes, 1‐butylimidazole was included as a monofunctional endcap …”

Section: Imidazolium Ionenesmentioning

confidence: 99%

See 1 more Smart Citation

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

Bara

O’Harra

2019

Macro Chemistry & Physics

View full text Add to dashboard Cite

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.

show abstract

“…Suckow et al explored the synthesis of imidazolium ionenes from “A‐B” monomers such as 1‐(6‐chlorohexyl)imidazole ( Scheme ) …”

Section: Imidazolium Ionenesmentioning

confidence: 99%

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

View full text Add to dashboard Cite

show abstract

“…MALDI-TOF MS was used to determine the number average molecular weight (M N ) and degree of polymerization (X N ) for the five new PAA and PAI ionenes. MALDI-TOF MS has been utilized with our previous imidazolium ionenes [ 9 , 10 , 12 , 13 , 36 ] and by other groups characterizing cationic ionenes, in order to analyze molecular weight [ 59 , 60 , 61 ]. A concentrated sample was prepared with DMAc, and multiple μL-sized spots were deposited onto the plate with different matrices (THAP, DCTB in MeOH) added following drying.…”

Section: Resultsmentioning

confidence: 99%

Designing Imidazolium Poly(amide-amide) and Poly(amide-imide) Ionenes and Their Interactions with Mono- and Tris(imidazolium) Ionic Liquids

et al. 2020

View full text Add to dashboard Cite

Here we introduce the synthesis and thermal properties of a series of sophisticated imidazolium ionenes with alternating amide-amide or amide-imide backbone functionality, and investigate the structural effects of mono(imidazolium) and unprecedented tris(imidazolium) ionic liquids (ILs) in these ionenes. The new set of poly(amide-amide) (PAA) and poly(amide-imide) (PAI) ionenes represent the intersection of conventional high-performance polymers with the ionene archetype–presenting polymers with alternating functional and ionic elements precisely sequenced along the backbone. The effects of polymer composition on the thermal properties and morphology were analyzed. Five distinct polymer backbones were synthesized and combined with a stoichiometric equivalent of the IL 1-benzyl-3-methylimidazolium bistriflimide ([Bnmim][Tf2N]), which were studied to probe the self-assembly, structuring, and contributions of intermolecular forces when IL is added. Furthermore, three polyamide (PA) or polyimide (PI) ionenes with simpler xylyl linkages were interfaced with [Bnmim][Tf2N] as well as a novel amide-linked tris(imidazolium) IL, to demonstrate the structural changes imparted by the inclusion of functional, ionic additives dispersed within the ionene matrix. This work highlights the possibilities for utilizing concepts from small molecules which exhibit supramolecular self-assembly to guide creative design and manipulate the structuring of ionenes.

show abstract

“…While polyaddition is less often applied for the preparation of PILs for membrane-based separation, the group of Prof. Drockenmuller has been investigating the possible synthesis routes, properties, and their further applications of 1,2,3-triazole-based PILs with triazolium cation in the main chain [ 190 , 191 , 192 , 193 , 194 , 195 ]. Suckow et al synthesized PILs from di-tertiary amines and alkyl dihalides in the attempts to prepare unidirectional polymers via polyaddition [ 196 ]. Nevertheless, triazole-based PILs have found little application in the form of gas separation membranes, although their selectivity was comparable to, or even exceeding the market standard for membrane-based CO 2 capture [ 197 ].…”

Section: Polymeric Ionic Liquids (Pils)mentioning

confidence: 99%

A Review on Ionic Liquid Gas Separation Membranes

et al. 2021

View full text Add to dashboard Cite

Ionic liquids have attracted the attention of the industry and research community as versatile solvents with unique properties, such as ionic conductivity, low volatility, high solubility of gases and vapors, thermal stability, and the possibility to combine anions and cations to yield an almost endless list of different structures. These features open perspectives for numerous applications, such as the reaction medium for chemical synthesis, electrolytes for batteries, solvent for gas sorption processes, and also membranes for gas separation. In the search for better-performing membrane materials and membranes for gas and vapor separation, ionic liquids have been investigated extensively in the last decade and a half. This review gives a complete overview of the main developments in the field of ionic liquid membranes since their first introduction. It covers all different materials, membrane types, their preparation, pure and mixed gas transport properties, and examples of potential gas separation applications. Special systems will also be discussed, including facilitated transport membranes and mixed matrix membranes. The main strengths and weaknesses of the different membrane types will be discussed, subdividing them into supported ionic liquid membranes (SILMs), poly(ionic liquids) or polymerized ionic liquids (PILs), polymer/ionic liquid blends (physically or chemically cross-linked ‘ion-gels’), and PIL/IL blends. Since membrane processes are advancing as an energy-efficient alternative to traditional separation processes, having shown promising results for complex new separation challenges like carbon capture as well, they may be the key to developing a more sustainable future society. In this light, this review presents the state-of-the-art of ionic liquid membranes, to analyze their potential in the gas separation processes of the future.

show abstract

Synthesis of polymeric ionic liquids with unidirectional chain topology by AB step growth polymerization

Cited by 16 publications

References 25 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

Designing Imidazolium Poly(amide-amide) and Poly(amide-imide) Ionenes and Their Interactions with Mono- and Tris(imidazolium) Ionic Liquids

A Review on Ionic Liquid Gas Separation Membranes

Contact Info

Product

Resources

About