Poly(1,2,3-triazolium imide)s Obtained Through AA + BB Click Polyaddition

Abstract

A series of poly(ionic liquid)s (PILs) incorporating 1,2,3-triazolium and imide units are synthesized in three steps by AA + BB polyaddition between α,ω-diazido tetraethylene glycol and three aromatic bis-imide dipropargyl monomers using copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) followed by N-alkylation of the resulting poly(1,2,3-triazole imide) s with iodomethane and subsequent anion exchange with lithium bis(trifluoromethylsulfonyl)imide. Structure/properties correlations of poly(1,2,3-triazole imide)s and corresponding poly(1,2,3-triazolium imide)s are discussed based on NMR spectroscopy, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), size exclusion chromatography (SEC) and solubility measurements.

Synthesis and Structure/Properties Correlations of Fluorinated Poly(1,2,3-triazolium)s

“…Poly(1,2,3-triazolium ionic liquid)s (PTILs) are a recent addition to broad PIL library [2,[26][27][28][29][30][31]. They are generally synthesized via copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), the most widespread example of the click chemistry philosophy [32].…”

“…Its experimental simplicity, reliability and robustness provides both ease of synthesis and broad structural design inspired from the extensive literature combining CuAAC with macromolecular engineering technologies [33][34][35][36]. Previously described PTILs include anionic polystyrene having covalently tethered TFSI anions and 1,2,3-triazolium counter cations [37], as well as cationic poly(meth)acrylates [38,39], polyvinyl esters [40], and main chain PTILs having a broad range of counter anions [2,[26][27][28][29][30][31]. Several PTILs with enhanced properties have shown promising performances in key-enabling technologies such as gas separation membranes [41,42], electrochromic devices [43,44], and as antibacterial or antifungal materials [45,46].…”