One-pot synthesis of poly(ionic liquid)s with 1,2,3-triazolium-based backbonesviaclickable ionic liquid monomers

Abstract

Clickable ionic liquid monomers realize the one-pot synthesis of ionically conducting poly(ionic liquid)s with 1,2,3-triazolium-based backbones via click chemistry.

Design of Clickable Ionic Liquid Monomers to Enhance Ionic Conductivity for Main-Chain 1,2,3-Triazolium-Based Poly(Ionic Liquid)s

“…All chemicals were used as received. Propargyl-TEG-OH, propargyl-MEG-iodide, and propargyl-TEG-iodide were synthesized as reported earlier. − IL monomer 1 and TPIL 4 were synthesized as described previously …”

“…38−40 IL monomer 1 and TPIL 4 were synthesized as described previously. 21 4.2. Characterization Methods.…”

“… 19 , 20 Inspired by these studies, we developed clickable α-azide-ω-alkyne IL monomers with a 1,2,3-triazolium cation and iodide(I) or bis(trifluoromethanesulfonyl)imide (Tf 2 N) counteranions and demonstrated the one-pot synthesis of backbone TPILs via click chemistry using clickable IL monomers. 21 Unlike the previous synthetic processes employed for TPIL preparation, our process is a one-step process for the synthesis of TPILs from the monomer, and the polymerization does not require solvents, polymerization mediators, or catalysts. However, the TPILs obtained using clickable IL monomers showed low ionic conductivities in the order of 10 –8 S cm –1 at 30 °C.…”

“…Among the various PILs reported to date, 1,2,3-triazolium-based PILs (TPILs) have been developed as a structurally rich family of PILs. , Their synthesis combines step-growth or chain-growth polymerization methods with copper-catalyzed azide–alkyne cycloaddition click chemistry using diazide and dialkyne or α-azide-ω-alkyne monomers, followed by a 1,2,3-triazole N -alkylation reaction. To date, a rich library of TPILs with tailored structures and properties ( e.g ., ionenes, poly­(acrylate)­s, poly­(vinyl ester)­s, poly­(styrene)­s, and poly­(siloxanes)) have been developed using efficient and orthogonal synthetic approaches. − Recently, Drockenmuller et al proposed to combine the thermal azide–alkyne cycloaddition of α-azide-ω-alkyne monomers with in situ N -alkylation of the generated poly­(1,2,3-triazole)­s using methyl iodide or N- methyl bis­(trifluoromethylsulfonyl)­imide as quaternizing agents. , Inspired by these studies, we developed clickable α-azide-ω-alkyne IL monomers with a 1,2,3-triazolium cation and iodide­(I) or bis­(trifluoromethanesulfonyl)­imide (Tf 2 N) counteranions and demonstrated the one-pot synthesis of backbone TPILs via click chemistry using clickable IL monomers . Unlike the previous synthetic processes employed for TPIL preparation, our process is a one-step process for the synthesis of TPILs from the monomer, and the polymerization does not require solvents, polymerization mediators, or catalysts.…”

Multilayer Poly(ionic liquid) Microcapsules Prepared by Sequential Phase Separation and Subsequent Photopolymerization in Ternary Emulsion Droplets

“…5−7 Additionally, they also showcase polymeric properties, such as processability and viscoelasticity. 1,7,8 These properties enable the usage of PILs in polyelectrolytes, 9−12 catalysis, 13−15 separation, 8,16,17 sensors, 18,19 actuator, 20,21 and CO 2 sorbents. 22−25 However, to incorporate PILs on a large scale into these applications, the development of novel technologies for processing PILs bulk into films, fibers, and particles is crucial.…”