Accelerated solvent- and catalyst-free synthesis of 1,2,3-triazolium-based poly(ionic liquid)s.
A straightforward and expeditious monotopic approach for the preparation of 1,2,3-triazolium-based poly(ionic liquids) (TPILs) is reported. It is based on the solvent- and catalyst-free polyaddition of an α-azide-ω-alkyne monomer in the presence of methyl iodide or N-methyl bis[(trifluoromethyl)sulfonyl]imide alkylating agents. Poly(1,2,3-triazole)s generated in bulk or by thermal azide-alkyne cycloaddition (AAC) are quaternized in-situ to afford TPILs composed of 1,3,4- and 1,3,5-trisubstituted 1,2,3-triazolium units. The physical and ion-conducting properties of the prepared samples are compared with the TPILs composed solely of 1,3,4-trisubstituted 1,2,3-triazolium units obtained through a multistep approach involving copper(I)-catalyzed AAC polyaddition, quaternization of the 1,2,3-triazole groups, and anion metathesis. TPILs obtained through the monotopic approach display thermal stabilities and ionic conductivities comparable to their pure regioisomeric analogues.
Université Claude Bernard Lyon 1, Ingénierie des Matériaux Polymères (UMR CNRS 5223), 15 Boulevard Latarjet, 69622, Villeurbanne Cedex, France.
Mona M
MM
Obadia
Bhanu P
BP
Mudraboyina
Imène
I
Allaoua
Ali
A
Haddane
Damien
D
Montarnal
Anatoli
A
Serghei
Eric
E
Drockenmuller
D000477:Alkylating Agents / Q000737:chemistry; D002384:Catalysis; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D052578:Ionic Liquids / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D008956:Models, Chemical; D015394:Molecular Structure; D011108:Polymers / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D012997:Solvents; D013237:Stereoisomerism; D013696:Temperature; D013997:Time Factors; D014230:Triazoles / Q000737:chemistry*
D000477:Alkylating Agents; D006847:Hydrocarbons, Iodinated; D052578:Ionic Liquids; D007477:Ions; D011108:Polymers; D012997:Solvents; D014230:Triazoles; C014055:methyl iodide
1,2,3-triazoliums; charge transport; click chemistry; poly(ionic liquid)s; polyaddition