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Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids

[Image: see text] Protic ionic liquids (PILs) are potential candidates as electrolyte components in energy storage devices. When replacing flammable and volatile organic solvents, PILs are expected to improve the safety and performance of electrochemical devices. Considering their technical applicat...

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Autores principales: de Araujo Lima e Souza, Giselle, Di Pietro, Maria Enrica, Castiglione, Franca, Marques Mezencio, Pedro Henrique, Fazzio Martins Martinez, Patricia, Mariani, Alessandro, Schütz, Hanno Maria, Passerini, Stefano, Middendorf, Maleen, Schönhoff, Monika, Triolo, Alessandro, Appetecchi, Giovanni Battista, Mele, Andrea
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9483912/
https://www.ncbi.nlm.nih.gov/pubmed/36039977
http://dx.doi.org/10.1021/acs.jpcb.2c02789
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author de Araujo Lima e Souza, Giselle
Di Pietro, Maria Enrica
Castiglione, Franca
Marques Mezencio, Pedro Henrique
Fazzio Martins Martinez, Patricia
Mariani, Alessandro
Schütz, Hanno Maria
Passerini, Stefano
Middendorf, Maleen
Schönhoff, Monika
Triolo, Alessandro
Appetecchi, Giovanni Battista
Mele, Andrea
author_facet de Araujo Lima e Souza, Giselle
Di Pietro, Maria Enrica
Castiglione, Franca
Marques Mezencio, Pedro Henrique
Fazzio Martins Martinez, Patricia
Mariani, Alessandro
Schütz, Hanno Maria
Passerini, Stefano
Middendorf, Maleen
Schönhoff, Monika
Triolo, Alessandro
Appetecchi, Giovanni Battista
Mele, Andrea
author_sort de Araujo Lima e Souza, Giselle
collection PubMed
description [Image: see text] Protic ionic liquids (PILs) are potential candidates as electrolyte components in energy storage devices. When replacing flammable and volatile organic solvents, PILs are expected to improve the safety and performance of electrochemical devices. Considering their technical application, a challenging task is the understanding of the key factors governing their intermolecular interactions and physicochemical properties. The present work intends to investigate the effects of the structural features on the properties of a promising PIL based on the 1,8-diazabicyclo[5.4.0]undec-7-ene (DBUH(+)) cation and the (trifluoromethanesulfonyl)(nonafluorobutanesulfonyl)imide (IM14(–)) anion, the latter being a remarkably large anion with an uneven distribution of the C–F pool between the two sides of the sulfonylimide moieties. For comparison purposes, the experimental investigations were extended to PILs composed of the same DBU-based cation and the trifluoromethanesulfonate (TFO(–)) or bis(trifluoromethanesulfonyl)imide (TFSI(–)) anion. The combined use of multiple NMR methods, thermal analyses, density, viscosity, and conductivity measurements provides a deep characterization of the PILs, unveiling peculiar behaviors in DBUH-IM14, which cannot be predicted solely on the basis of differences between aqueous pK(a) values of the protonated base and the acid (ΔpK(a)). Interestingly, the thermal and electrochemical properties of DBUH-IM14 turn out to be markedly governed by the size and asymmetric nature of the anion. This observation highlights that the structural features of the precursors are an important tool to tailor the PIL’s properties according to the specific application.
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spelling pubmed-94839122022-09-20 Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids de Araujo Lima e Souza, Giselle Di Pietro, Maria Enrica Castiglione, Franca Marques Mezencio, Pedro Henrique Fazzio Martins Martinez, Patricia Mariani, Alessandro Schütz, Hanno Maria Passerini, Stefano Middendorf, Maleen Schönhoff, Monika Triolo, Alessandro Appetecchi, Giovanni Battista Mele, Andrea J Phys Chem B [Image: see text] Protic ionic liquids (PILs) are potential candidates as electrolyte components in energy storage devices. When replacing flammable and volatile organic solvents, PILs are expected to improve the safety and performance of electrochemical devices. Considering their technical application, a challenging task is the understanding of the key factors governing their intermolecular interactions and physicochemical properties. The present work intends to investigate the effects of the structural features on the properties of a promising PIL based on the 1,8-diazabicyclo[5.4.0]undec-7-ene (DBUH(+)) cation and the (trifluoromethanesulfonyl)(nonafluorobutanesulfonyl)imide (IM14(–)) anion, the latter being a remarkably large anion with an uneven distribution of the C–F pool between the two sides of the sulfonylimide moieties. For comparison purposes, the experimental investigations were extended to PILs composed of the same DBU-based cation and the trifluoromethanesulfonate (TFO(–)) or bis(trifluoromethanesulfonyl)imide (TFSI(–)) anion. The combined use of multiple NMR methods, thermal analyses, density, viscosity, and conductivity measurements provides a deep characterization of the PILs, unveiling peculiar behaviors in DBUH-IM14, which cannot be predicted solely on the basis of differences between aqueous pK(a) values of the protonated base and the acid (ΔpK(a)). Interestingly, the thermal and electrochemical properties of DBUH-IM14 turn out to be markedly governed by the size and asymmetric nature of the anion. This observation highlights that the structural features of the precursors are an important tool to tailor the PIL’s properties according to the specific application. American Chemical Society 2022-08-30 2022-09-15 /pmc/articles/PMC9483912/ /pubmed/36039977 http://dx.doi.org/10.1021/acs.jpcb.2c02789 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle de Araujo Lima e Souza, Giselle
Di Pietro, Maria Enrica
Castiglione, Franca
Marques Mezencio, Pedro Henrique
Fazzio Martins Martinez, Patricia
Mariani, Alessandro
Schütz, Hanno Maria
Passerini, Stefano
Middendorf, Maleen
Schönhoff, Monika
Triolo, Alessandro
Appetecchi, Giovanni Battista
Mele, Andrea
Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title_full Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title_fullStr Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title_full_unstemmed Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title_short Implications of Anion Structure on Physicochemical Properties of DBU-Based Protic Ionic Liquids
title_sort implications of anion structure on physicochemical properties of dbu-based protic ionic liquids
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9483912/
https://www.ncbi.nlm.nih.gov/pubmed/36039977
http://dx.doi.org/10.1021/acs.jpcb.2c02789
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