Better Than the Best Polar Solvent: Tuning the Polarity of 1,2,4‐ Triazolium‐Based Ionic Liquids

Singh, Dharmendra; Sharma, Gyanendra; Gardas, Ramesh L.

doi:10.1002/slct.201700639

Cited by 11 publications

(7 citation statements)

References 38 publications

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“…Last year, we proposed triazolium-based ILs as a novel class of cellulose solvents [38]. This class of ILs has been discussed in the literature earlier [1,19,21,42,43], but had never been applied to dissolve cellulose before. The 1,2,3-triazolium cation is very similar to imidazolium; only a C-H fragment in the aromatic ring is replaced by a nitrogen atom.…”

Section: Introductionmentioning

confidence: 99%

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

et al. 2020

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We present 1,2,3-triazolium- and imidazolium-based ionic liquids (ILs) with aromatic anions as a new class of cellulose solvents. The two anions in our study, benzoate and salicylate, possess a lower basicity when compared to acetate and therefore should lead to a lower amount of N-heterocyclic carbenes (NHCs) in the ILs. We characterize their physicochemical properties and find that all of them are liquids at room temperature. By applying force field molecular dynamics (MD) simulations, we investigate the structure and dynamics of the liquids and find strong and long-lived hydrogen bonds, as well as significant π–π stacking between the aromatic anion and cation. Our ILs dissolve up to 8.5 wt.-% cellulose. Via NMR spectroscopy of the solution, we rule out chain degradation or derivatization, even after several weeks at elevated temperature. Based on our MD simulations, we estimate the enthalpy of solvation and derive a simple model for semi-quantitative prediction of cellulose solubility in ILs. With the help of Sankey diagrams, we illustrate the hydrogen bond network topology of the solutions, which is characterized by competing hydrogen bond donors and acceptors. The hydrogen bonds between cellulose and the anions possess average lifetimes in the nanosecond range, which is longer than found in common pure ILs.

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Section: Introductionmentioning

confidence: 99%

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

et al. 2020

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“…In this perceptive we also predicted the correlation between refractive indices ( n D ) and polarity (

E_{T}^{N}

) parameters of studied PILs. A recent study by our group was also carried out to provide a positive correlation between n D and

E_{T}^{N}

parameters of 1,2,4‐triazolium class of ILs . As illustrated in Figure , the polarity (

E_{T}^{N}

) parameter are found to decrease with the progression of refractive indices of studied PILs.…”

Section: Resultsmentioning

confidence: 82%

Influence of Alkyl Substituent on Optical Properties of Carboxylate-Based Protic Ionic Liquids

et al. 2017

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The solvation strength of N,N‐dialkylethanolammonium based protic ionic liquids (PILs) have been determined by normalised Reichardt's parameter (ETN ) and molecular polarizability (αP). The solvation strength depends on the intermolecular interactions which are governed by the functional group and molecular structure of the species. So here in this work, the influence of functional groups such as –OH, –RCOOH and –R, on solvatochromic parameters of studied PILs have been discussed in terms of experimental results and relevant literature. Further the intermolecular interactions of PILs have been analyzed with the help of temperature dependant experimental refractive index data. Additionally, a positive correlation was obtained between the polarity and the refractive index of the studied PILs.

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“…Though, few glyme‐based ILs showed polarity slightly higher than water (having =1.03) but most of the ILs available in open literature have polarities lies in the range of (0.50–0.75) . In this regards, our previous reports demonstrate the high polarity of 1,2,4‐triazolium based ILs and the effect of temperature on polarity . ILs having better polarity than water consequence of extent of coulombic and vander Waal's interactions between ions.…”

Section: Resultsmentioning

confidence: 84%

Effect of Fluorinated Anion on the Physicochemical, Rheological and Solvatochromic Properties of Protic and Aprotic Ionic Liquids: Experimental and Computational Study

2017

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The essential properties of ionic liquids (ILs) for various applications can be tuned by changing the combination of cations or anions in ILs. This work demonstrates how the structure variations effect the physicochemical, rheological and solvatochromic properties of protic and aprotic ionic liquids. For this, a set of four ionic liquids have been synthesized and characterized through spectral techniques. Thermal stability and phase behaviour of ILs have been analyzed by TGA and DSC. The experimental density, speed of sound and viscosity have been measured as a function of temperature from 293.15 to 343.15 K and an attempt has been made to distinguish the crucial role of counter ions on measured properties. Further, the fluidity and polarity behaviour of hydroxyl ammonium based protic or 1‐alkyl‐1,2,4‐triazolium based aprotic cation and fluorinated anions were investigated through their rheological and polarity parameters at 298.15 K and discussion have been made on the basis of columbic and hydrogen bonding interactions. Interestingly, we found that anions have dominant effect on studied physicochemical properties irrespective of protic/aprotic nature of ionic liquid while the contribution of cations were vital for solvatochromic and rheological properties. Additionally, the ion‐pair interaction energy, dipole moment and hydrogen bonding interactions of studied ILs have been analysed using density functional theory (DFT) calculations to support the experimental findings.

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Better Than the Best Polar Solvent: Tuning the Polarity of 1,2,4‐ Triazolium‐Based Ionic Liquids

Cited by 11 publications

References 38 publications

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

Dissolving Cellulose in 1,2,3-Triazolium- and Imidazolium-Based Ionic Liquids with Aromatic Anions

Influence of Alkyl Substituent on Optical Properties of Carboxylate-Based Protic Ionic Liquids

Effect of Fluorinated Anion on the Physicochemical, Rheological and Solvatochromic Properties of Protic and Aprotic Ionic Liquids: Experimental and Computational Study

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