Biosourced 1,2,3-triazolium ionic liquids derived from isosorbide

Abstract

International audienceTwo series of 1,2,3-triazolium chiral ionic liquid (CIL) stereoisomers are synthesized from isosorbide by combining the robust attributes of the copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), alkylation of the resulting 1,2,3-triazoles by methyl iodide and further anion metathesis with different fluorinated salts. These novel biosourced CILs are characterized in details by H-1 and C-13 NMR spectroscopy, high-resolution mass spectrometry (ESI-HRMS), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and broadband dielectric spectroscopy (BDS). The effect of stereochemistry on their physical, thermal and ion conducting properties is discussed. Markedly, it is demonstrated for the first time that stereochemistry can drastically influence ionic conductivity by several orders of magnitude

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

“…43,44 Although anterior but limited in scope preparation methods exist, CuAAC ligation is now a mainstream synthetic tool to access 1,2,3-triazoles of varied complexity and functionality. [45][46][47][48] This robust, efficient and tolerant reaction has an extremely wide scope, occurs under mild conditions and only necessitates straightforward isolation and purification methods. The variety of TILs (i.e.…”

Synthesis and antioxidant action of chitosan derivatives with amino-containing groups via azide-alkyne click reaction and N-methylation

“…Besides, the other newly formed characteristic proton signals of methylene of chitosan derivatives bearing 1,2,3-triazole at 4.65 and 4.29 ppm (b in the spectra of chitosan derivatives 7a and 7b) and 3.53, 3.50, and 3.54 ppm (c in the spectra of chitosan derivatives 7a, 7b, and 7c) are also observed. Moreover, after the methylation, the characteristic resonances located at 8.03-8.48 ppm for the protons of 1,2,3triazole groups weaken greatly and new peaks at 8.69, 8.84, and 8.72 ppm (a in the spectra of chitosan derivatives 9a, 9b, and 9c) and 4.26, 4.35, and 4.31 ppm (d in the spectra of chitosan derivatives 9a, 9b, and 9c) are respectively assigned to the resonance of 5-H position of 1,2,3-triazolium rings and the pendant methyl groups attached to the nitrogen of 1,2,3-triazolium moieties (Abdelhedi-Miladi et al, 2014;M'Sahel et al, 2016). Besides, it is worth noting that the proton signals of methylene (b and c in the spectra of chitosan derivatives 9a, 9b, and 9c) are also shifted towards down field compared to those initially neighboring the 1,2,3-triazole groups.…”

Ion Transport Properties and Ionicity of 1,3-Dimethyl-1,2,3-Triazolium Salts with Fluorinated Anions

“…Figure S13 ), and the respective values of the molar mass ( Λ = σ 0 × M/ρ ). Figure 3 shows the temperature-dependent molar ion conductivity of [DMTR][OTf] and [DMTR][NTf 2 ], which can be described with the Vogel–Fulcher–Tammann (VFT) equation by [ 18 , 38 ]: where Λ ∞ is the limit of the conductivity at infinite high temperatures directly related to the number of charge carriers [ 38 ], E a the activation energy for charge transport, R is the universal gas constant, and T 0 the Vogel temperature. In complete analogy to the values of Λ , a larger value of Λ ∞ is also obtained for the TRS bearing the large [NTf 2 ] − anion (cf.…”

“…Imidazolium salts are the golden standard at the moment [ 2 ] but 1,2,3-triazolium salts (TRSs) are a class of ILs which receive continuously increasing interest due to their facile accessibility via Cu(I)-catalyzed Huisgen-type 1,3-dipolar cycloaddition (CuAAC, “click” reaction), and subsequent N -alkylation in quantitative yields [ 1 , 3 , 4 , 5 , 6 ]. Optionally, the anion can be exchanged in an additional so-called salt metathesis step [ 1 ], which enables different combinations of cations and anions for TRSs with tuneable properties for a plethora of applications as reaction media [ 7 , 8 ], antifungal agents [ 9 , 10 ], molecular machines [ 11 , 12 ], sensors [ 13 ], anticancer drugs [ 14 ], precursors for N -heterocyclic carbene ligands [ 15 , 16 ], or electrolyte systems in electrochemical devices such as batteries, fuel cells, transistors, and solar cells [ 17 , 18 , 19 , 20 ].…”