TY - JOUR
T1 - Design of Clickable Ionic Liquid Monomers to Enhance Ionic Conductivity for Main-Chain 1,2,3-Triazolium-Based Poly(Ionic Liquid)s
AU - Hirai, Ruka
AU - Watanabe, Takaichi
AU - Ono, Tsutomu
N1 - Funding Information:
This work was financially supported by the JSPS KAKENHI (grant nos. JP18H03854 and JP19K15340). The authors thank Associated Professor Takashi Teranishi (Okayama University) for ionic conductivity measurements. They also thank Division of Instrumental Analysis, Okayama University, for H NMR measurements and acknowledge Yu Mitsuoka and Motonari Kobayashi for C NMR measurements and elemental analyses, respectively. 1 13
Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society.
PY - 2021/4/20
Y1 - 2021/4/20
N2 - A series of clickable α-azide-ω-alkyne ionic liquid (IL) monomers with an ethylene oxide spacer were developed and applied to the synthesis of 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) with high ionic conductivities via one-step thermal azide-alkyne cycloaddition click chemistry. Subsequently, the number of IL moieties in the resultant TPILs was further increased by N-alkylation of the 1,2,3-triazole-based backbones of the TPILs with a quarternizing reagent. This strategy affords the preparation of TPILs having either one or two 1,2,3-triazolium cations with bis(trifluoromethylsulfonyl)imide anions in a monomer unit. Synthesis of the TPILs was confirmed by 1H and 13C NMR spectroscopy and gel permeation chromatography. The effects of the length of the ethylene oxide spacer and the number of IL moieties in the IL monomer unit on the physicochemical properties of the TPILs were characterized by differential scanning calorimetry, thermogravimetric analysis, and impedance spectroscopy. The introduction of a longer ethylene oxide spacer or an increase in the number of IL moieties in the monomer unit resulted in TPILs with lower glass-transition temperatures and higher ionic conductivities. The highest ionic conductivity achieved in this study was 2.0 × 10-5 S cm-1 at 30 °C. These results suggest that the design of the IL monomer provides the resultant polymer with high chain flexibility and a high IL density, and so it is effective for preparing TPILs with high ionic conductivities.
AB - A series of clickable α-azide-ω-alkyne ionic liquid (IL) monomers with an ethylene oxide spacer were developed and applied to the synthesis of 1,2,3-triazolium-based poly(ionic liquid)s (TPILs) with high ionic conductivities via one-step thermal azide-alkyne cycloaddition click chemistry. Subsequently, the number of IL moieties in the resultant TPILs was further increased by N-alkylation of the 1,2,3-triazole-based backbones of the TPILs with a quarternizing reagent. This strategy affords the preparation of TPILs having either one or two 1,2,3-triazolium cations with bis(trifluoromethylsulfonyl)imide anions in a monomer unit. Synthesis of the TPILs was confirmed by 1H and 13C NMR spectroscopy and gel permeation chromatography. The effects of the length of the ethylene oxide spacer and the number of IL moieties in the IL monomer unit on the physicochemical properties of the TPILs were characterized by differential scanning calorimetry, thermogravimetric analysis, and impedance spectroscopy. The introduction of a longer ethylene oxide spacer or an increase in the number of IL moieties in the monomer unit resulted in TPILs with lower glass-transition temperatures and higher ionic conductivities. The highest ionic conductivity achieved in this study was 2.0 × 10-5 S cm-1 at 30 °C. These results suggest that the design of the IL monomer provides the resultant polymer with high chain flexibility and a high IL density, and so it is effective for preparing TPILs with high ionic conductivities.
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U2 - 10.1021/acsomega.0c06173
DO - 10.1021/acsomega.0c06173
M3 - Article
AN - SCOPUS:85105084942
VL - 6
SP - 10030
EP - 10038
JO - ACS Omega
JF - ACS Omega
SN - 2470-1343
IS - 15
ER -