1,2,3‐Triazolium‐Based Poly(ionic liquid)s Obtained Through Click Chemistry Polyaddition

Abstract

A series of four 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) is synthesized from the polyaddition of different tailor-made α-azide-ω-alkyne monomers by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), followed by quaternization with methyl iodide and subsequent anion exchange with lithium bis(trifl uoromethylsulfonyl)imide. Whereas the chemical structures of the bis(trifl uoromethylsulfonyl)imide counter anion and the N -3 methyl group are common to all TPILs, the structural features of the repeating units, i.e., triethylene glycol or undecanoyl spacers with either ester or ether linkages, are varied and compared. Their impact on the physical and ion-conducting properties of the obtained TPILs is established based on 1 H NMR, DSC, thermogravimetric analysis (TGA), and broadband di electric spectroscopy (BDS) characterization techniques. Most importantly, the replacement of an ether by an ester group at the C -4 position of the 1,2,3-triazolium ring signifi cantly decreases the thermal stability and ionic conductivity of TPILs, whereas the chemical nature of the triethylene glycol or undec anoyl spacers has little infl uence on the materials properties.

Triethylene glycol-based poly(1,2,3-triazolium acrylate)s with enhanced ionic conductivity

“…However, the nature of the spacer does not affect thermal properties of poly(1,2,3-triazolium acrylate)s since an aliphatic analogue of 7 having a nC 11 H 22 spacer has T g and T d10 values of −36 and 203°C, respectively. The values are in close agreement with those of PTILs having a nC 11 H 22 side chain spacer (T g from −48 to Table 1 Physical properties of azide-functionalized polyacrylate 4, 1,2,3-triazole-funtionalized polyacrylate 6, and poly(1,2,3-triazolium acrylate)s 7-10 −20°C), 27 a main chain nC 11 H 22 spacer (T g from −68 to +5°C), 23,26 or a main chain TEG-based spacer (T g from −48 to +5°C). The change in counter anion induces a slight shift in the 1 H NMR signal of the 1,2,3-triazolium proton from 8.87 ppm for 7 to 8.67, 8.70 and 8.74 ppm for 8-10, respectively (Fig.…”

“…20,21 A broad library of PILs has been established by combining cationic moieties (e.g. [23][24][25][26][27][28][29][30][31] Thanks to the robustness of the developed synthetic routes, a significantly broad library of PTILs with high thermal stability, low T g and high ionic conductivity has been developed through extensive macromolecular design, combinations of different anions, polymer backbones and architectures thus unfolding the potential of this new family of PILs. halides, sulfonates, carbonates, inorganic fluorides, perfluorinated sulfonimides, tricyanomethanide or dicyanamide).…”

“…ammonium, pyridinium, imidazolium, pyrrolidinium, phosphonium or 1,2,3-triazolium) with anionic counterparts (e.g. PTIL ionenes obtained by step growth polymerization, [23][24][25][26] as well as polyacrylate, 27 polystyrene, 28 poly(vinyl ester), 31 and poly-(4vinyl-1,2,3-triazolium), 18,32 PTILs obtained by chain growth polymerizations have been reported so far. Cationic PILs having free counter anions have been predominantly explored compared to their anionic and zwitterionic analogues.…”

Design, synthesis of novel starch derivative bearing 1,2,3-triazolium and pyridinium and evaluation of its antifungal activity

“…13 C NMR spectrum of starch derivative (III) (Fig. 3) also corroborates the alkylation since signals corresponding to 1,2,3-triazolium carbons at 140.23 and 128.30 ppm and the methyl group at 33.20 ppm are observed together with the total disappearance of the 1,2,3-triazole carbon signals initially located at 144.72 and 124.92 ppm (Abdelhedi-Miladi et al, 2014). Most other carbon signals are shifted after alkylation of the 1,2,3-triazole and pyridine rings.…”

Novel 1,2,3-triazolium-functionalized starch derivatives: Synthesis, characterization, and evaluation of antifungal property

“…The antibacterial-starch biomaterials could be obtained by anchoring the strong electron-withdrawing groups onto the starch backbone by the CuAAC reaction . Very recently, the synthesis of 1,2,3-triazolium groups by Nalkylating 1,2,3-triazole with alkyl halides begins to be paid close attention as they combine the interesting properties of ionic liquids and the versatile mechanical and broad-spectrum properties and applications of polymers and catalysis (Abdelhedi-Miladi et al, 2014;Mudraboyina et al, 2014;Ohmatsu, Hamajima, & Ooi, 2012). However, although the 1,2,3-triazole-linked starch derivatives have been reported and described, to date there are surprisingly very few reports describing the preparation of starch derivatives bearing 1,2,3-triazolium.…”