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Akacha, Rania
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document
1,3,4,5‐Tetrasubstituted Poly(1,2,3‐triazolium) Obtained through Metal‐Free AA+BB Polyaddition of a Diazide and an Activated Internal Dialkyne
Abstract
<jats:title>Abstract</jats:title><jats:p>A tetra(ethylene glycol)‐based 1,3,4,5‐tetrasubstituted poly(1,2,3‐triazolium) is synthesized in two steps including: i) the catalyst‐free polyaddition of a diazide and an activated internal dialkyne and ii) the <jats:italic>N</jats:italic>‐alkylation of the resulting 1,2,3‐triazole groups. In order to provide detailed structure/properties correlations different analogs are also synthesized. First, parent poly(1,2,3‐triazole)s are obtained via AA+BB polyaddition using copper(I)‐catalyzed alkyne‐azide cycloaddition or metal‐free thermal alkyne‐azide cycloaddition (TAAC). Poly(1,2,3‐triazole)s with higher molar masses are obtained in higher yields by TAAC polyaddition. A 1,3,4‐trisubstituted poly(1,2,3‐triazolium) structural analog obtained by TAAC polyaddition using a terminal activated dialkyne and subsequent <jats:italic>N</jats:italic>‐alkylation of the 1,2,3‐triazole groups enables discussing the influence of the methyl group in the C‐4 or C‐5 position on thermal and ion conducting properties. Obtained polymers are characterized by <jats:sup>1</jats:sup>H, <jats:sup>13</jats:sup>C, and <jats:sup>19</jats:sup>F NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, size exclusion chromatography, and broadband dielectric spectroscopy. The targeted 1,3,4,5‐tetrasubstituted poly(1,2,3‐triazolium) exhibits a glass transition temperature of −23 °C and a direct current ionic conductivity of 2.0 × 10<jats:sup>−6</jats:sup> S cm<jats:sup>−1</jats:sup> at 30 °C under anhydrous conditions. The developed strategy offers opportunities to further tune the electron delocalization of the 1,2,3‐triazolium cation and the properties of poly(1,2,3‐triazolium)s using this additional substituent as structural handle.</jats:p>