Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids
Benzimidazole dicationic ionic liquids (BDILs) have not yet been widely explored in spite of their potential. Therefore, two structurally related families of BDILs, paired with either bromide or bistriflimide anions and bearing alkyl spacers ranging from C3 to C6, have been prepared. Their thermal p...
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doaj-516e02e4ef584acd9c6185232ad0979b2021-07-23T13:56:27ZengMDPI AGMolecules1420-30492021-07-01264211421110.3390/molecules26144211Expanding the Chemical Space of Benzimidazole Dicationic Ionic LiquidsAndrea Mezzetta0Luca Guglielmero1Angelica Mero2Giorgio Tofani3Felicia D’Andrea4Christian Silvio Pomelli5Lorenzo Guazzelli6Department of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyDepartment of Pharmacy, University of Pisa, Via Bonanno 33, 56126 Pisa, ItalyBenzimidazole dicationic ionic liquids (BDILs) have not yet been widely explored in spite of their potential. Therefore, two structurally related families of BDILs, paired with either bromide or bistriflimide anions and bearing alkyl spacers ranging from C3 to C6, have been prepared. Their thermal properties have been studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), while their electrical properties have been assessed by cyclic voltammetry (CV). TG analysis confirmed the higher stability of the bistriflimide BDILs over the bromide BDILs, with minor variation within the two families. Conversely, DSC and CV allowed for ascertaining the role played by the spacer length. In particular, the thermal behavior changed dramatically among the members of the bistriflimide family, and all three possible thermal behavior types of ILs were observed. Furthermore, cyclic voltammetry showed different electrochemical window (C<sub>3</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N < C<sub>4</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N, C<sub>5</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N < C<sub>6</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N) as well as a reduction peak potential, shape, and intensity as a function of the spacer length. The results obtained highlight the benefit of accessing a more structurally diverse pool of compounds offered by dicationic ILs when compared to the parent monocationic ILs. In particular, gains are to be found in the ease of fine-tuning their properties, which translates in facilitating further investigations toward BDILs as designer solvents and catalysts.https://www.mdpi.com/1420-3049/26/14/4211ionic liquidsgreen solventsbenzimidazoledicationic ionic liquidsthermal stabilitythermal behavior |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Andrea Mezzetta Luca Guglielmero Angelica Mero Giorgio Tofani Felicia D’Andrea Christian Silvio Pomelli Lorenzo Guazzelli |
spellingShingle |
Andrea Mezzetta Luca Guglielmero Angelica Mero Giorgio Tofani Felicia D’Andrea Christian Silvio Pomelli Lorenzo Guazzelli Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids Molecules ionic liquids green solvents benzimidazole dicationic ionic liquids thermal stability thermal behavior |
author_facet |
Andrea Mezzetta Luca Guglielmero Angelica Mero Giorgio Tofani Felicia D’Andrea Christian Silvio Pomelli Lorenzo Guazzelli |
author_sort |
Andrea Mezzetta |
title |
Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids |
title_short |
Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids |
title_full |
Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids |
title_fullStr |
Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids |
title_full_unstemmed |
Expanding the Chemical Space of Benzimidazole Dicationic Ionic Liquids |
title_sort |
expanding the chemical space of benzimidazole dicationic ionic liquids |
publisher |
MDPI AG |
series |
Molecules |
issn |
1420-3049 |
publishDate |
2021-07-01 |
description |
Benzimidazole dicationic ionic liquids (BDILs) have not yet been widely explored in spite of their potential. Therefore, two structurally related families of BDILs, paired with either bromide or bistriflimide anions and bearing alkyl spacers ranging from C3 to C6, have been prepared. Their thermal properties have been studied by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC), while their electrical properties have been assessed by cyclic voltammetry (CV). TG analysis confirmed the higher stability of the bistriflimide BDILs over the bromide BDILs, with minor variation within the two families. Conversely, DSC and CV allowed for ascertaining the role played by the spacer length. In particular, the thermal behavior changed dramatically among the members of the bistriflimide family, and all three possible thermal behavior types of ILs were observed. Furthermore, cyclic voltammetry showed different electrochemical window (C<sub>3</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N < C<sub>4</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N, C<sub>5</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N < C<sub>6</sub>(C<sub>1</sub>BenzIm)<sub>2</sub>/2Tf<sub>2</sub>N) as well as a reduction peak potential, shape, and intensity as a function of the spacer length. The results obtained highlight the benefit of accessing a more structurally diverse pool of compounds offered by dicationic ILs when compared to the parent monocationic ILs. In particular, gains are to be found in the ease of fine-tuning their properties, which translates in facilitating further investigations toward BDILs as designer solvents and catalysts. |
topic |
ionic liquids green solvents benzimidazole dicationic ionic liquids thermal stability thermal behavior |
url |
https://www.mdpi.com/1420-3049/26/14/4211 |
work_keys_str_mv |
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1721286871868243968 |