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Issue 1, 2016
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Biosourced 1,2,3-triazolium ionic liquids derived from isosorbide

Malek M'sahel,abc  Mona Marie Obadia,a  Raouf Medimagh,*b  Anatoli Serghei,a  Mongia Said Zinac  and  Eric Drockenmuller*a 
Author affiliations

* Corresponding authors

a Laboratoire d'Ingénierie des Matériaux Polymères (UMR CNRS 5223), Université Claude Bernard Lyon 1, 15 Boulevard Latarjet, 69622 Villeurbanne Cedex, France
E-mail: eric.drockenmuller@univ-lyon1.fr

b Laboratoire des Substances Naturelles (LR10INRAP02), Institut National de Recherche et d'Analyse Physico-chimique, Sidi Thabet Biotechpole, 2020 Ariana, Tunisia
E-mail: raouf.medimagh@inrap.rnrt.tn

c Faculté des Sciences de Tunis El Manar, Université de Tunis, El Manar, Tunisia

Abstract

Two 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 1H and 13C 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.

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

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Publication details

The article was received on 29 Sep 2015, accepted on 12 Nov 2015 and first published on 16 Nov 2015


Article type: Paper
DOI: 10.1039/C5NJ02660A
Citation: New J. Chem., 2016,40, 740-747
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    Biosourced 1,2,3-triazolium ionic liquids derived from isosorbide

    M. M'sahel, M. M. Obadia, R. Medimagh, A. Serghei, M. Said Zina and E. Drockenmuller, New J. Chem., 2016, 40, 740
    DOI: 10.1039/C5NJ02660A

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