A series of six 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) having random distributions of 1,3,4- and 1,3,5-trisubstituted 3-methyl-1,2,3-triazolium units are prepared by the solvent- and catalyst-free 1,3-dipolar Huisgen cycloaddition of two α-azide-ω-alkyne monomers and simultaneous N-alkylation of the resulting 1,4- and 1,5-disubstituted poly(1,2,3-triazole)s by N-methyl bis(trifluoromethylsulfonyl)imide (TFSI), trimethyl phosphate or methyl methanesulfonate quaternizing agents. The physical and ion conducting properties of this series of TPILs having TFSI, dimethyl phosphate (DMP) or methanesulfonate (MSF) anions are discussed based on solubility, differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), size exclusion chromatography (SEC) and broadband dielectric spectroscopy (BDS) measurements.