Versatile click functionalization of poly(1,2,3-triazolium ionic liquid)s

Mudraboyina, Bhanu P.; Obadia, Mona M.; Abdelhedi-Miladi, Imen; Allaoua, Imène; Drockenmuller, Éric

doi:10.1016/j.eurpolymj.2014.08.025

Cited by 34 publications

(22 citation statements)

References 29 publications

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“…19). 117 The fraction of randomly distributed alkyne pendant groups could be readily tuned from 100 mol% of 1,2,3-triazolium units ( This original two-step Nalkylation/CuAAC sequence could be extrapolated to iterative synthetic approaches, [118][119][120][121] by further repeating this reaction sequence since each newly formed 1,2,3-triazole group generated after CuAAC coupling can be submitted to additional N-alkylation. For instance, a polymer template carrying a single clickable functionality could yield a multifunctionalized derivative by multiple regeneration of a clickable functionality after N-alkylation of the newly formed 1,2,3-triazoles.…”

Section: N-alkylation Of 123-triazoles To Introduce Pendant Clickabmentioning

confidence: 99%

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

2016

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Poly(ionic liquid)s (PILs) are a unique class of polyelectrolytes having properties suited for modern technological applications such as electrochemical devices (batteries, supercapacitors, light-emitting electrochemical cells), ion-gated field effect transistors, electrochromic devices, fuel cells, dye sensitized solar cells, catalysis, or soft robotics. Their structure and properties can be finely tuned by unlimited combinations issued from extended pools of cationic and anionic building blocks. In a constant quest for the development of solid polymer electrolytes with enhanced physical, mechanical and (electro)chemical properties, a new class of PILs based on 1,2,3-triazolium cations has been recently developed. Their preparation takes advantage of the beneficial features of the multiple combinations between the Click chemistry philosophy with macromolecular engineering techniques to afford tunable and highly functional ion conducting materials thus stretching out the actual boundaries of PILs macromolecular design. This feature article summarizes the different strategies developed so far for the synthesis of 1,2,3-triazolium-based PILs (TPILs) since their first introduction in 2013.

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Section: N-alkylation Of 123-triazoles To Introduce Pendant Clickabmentioning

confidence: 99%

Poly(1,2,3-triazolium)s: a new class of functional polymer electrolytes

2016

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“…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).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2015

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International audienceA series of cationic poly(acrylate ionic liquid)s having a triethylene glycol (TEG) spacer and a pendant 1,2,3-triazolium group is synthesized by post-polymerization sequential chemical modifications. A chloride-functionalized polyacrylate common precursor is first obtained by reversible addition-fragmentation chain transfer (RAFT) polymerization of a TEG-based chloride-functionalized acrylate. Sequential azidation, copper-catalyzed azide-alkyne cycloaddition with 1-pentyne and alkylation of the resulting 1,2,3-triazole by methyl iodide affords a poly(acrylate ionic liquid) having pendant 3-methyl-4-propyl-1,2,3-triazolium iodide groups. Further anion metathesis with three different fluorinated salts yields a series of 1,2,3-triazolium-based PILs with distinct counter anions. The polymer precursors and resulting poly(1,2,3-triazolium ionic liquid) s (PTILs) are characterized by H-1 NMR spectroscopy, size exclusion chromatography (SEC), differential scanning calorimetry (DSC), thermogravimetric analysis (TGA) and broadband dielectric spectroscopy (BDS). Well-defined PTIL derivative with bis(trifluoromethane) sulfonimide anion (M-n = 113,600 g mol(-1) and D = 1.23) exhibits the lowest glass transition temperature (T-g = -36 degrees C), the highest thermal stability (T-d10 = 321 degrees C) and the highest anhydrous ionic conductivity (sigma(DC) = 1.1 x 10(-5) S cm(-1) at 30 degrees C) of the series

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“…However, native starch can not meet the demands for further industrial applications on account of lacking active groups 2014; Zhang, Wei, Vijaya Kumar, Rasheed, & Zhou, 2014), anticancer (Kumar et al, 2011), antimalarial (Pereira et al, 2014), and antioxidant (Tan, Li, Li, Dong & Guo, 2016), have also facilitated the chemical modification of polysaccharide with 1,2,3-triazoles. Meanwhile, alkylation of 1,2,3-triazoles can provide the 1,2,3-triazolium cations, which have been prepared for novel ionic liquids (Mudraboyina, Obadia, Abdelhedi-Miladi, Allaoua, & Drockenmuller, 2015;Obadia, Crépet, Serghei, Montarnal, & Drockenmuller, 2015;Obadia et al, 2014) and catalysts (Aizpurua et al, 2014;Jha & Jain, 2013;Ohmatsu, Hamajima, & Ooi, 2012) because of high thermal stability, tunable solubility, and low flammability . However, although the 1,2,3-triazole-linked starch derivatives have been reported and described, to our knowledge there are no reports on synthesis and bioactivity of starch derivatives bearing 1,2,3-triazolium cations so far.…”

Section: Introductionmentioning

confidence: 99%