Examining the interactions of a thermally robust task-specific phosphonium-based ionic compound

Teodoro, Lara I.; Bellia, Sophia; Zeller, Mat­thias; Hillesheim, Patrick C.

doi:10.1016/j.cdc.2021.100760

Cited by 4 publications

(5 citation statements)

References 60 publications

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“…While IL chemists mostly rely on computational approaches to gain an enhanced understanding of intermolecular interactions within IL systems and the conformational states of each component of the salt, it is noteworthy that comparable methods taking advantage of crystallographic studies have been scarcely addressed . Herein, we expand upon our previous works on TPP-derived ionic materials by reporting the synthesis and characterization of four TPP-based ILs containing perfluoroalkyl anions (Figure ). The thermal properties of the compounds are examined via thermogravimetric analysis (TGA) and dynamic scanning calorimetry (DSC) and the results of the thermal studies correlated to their crystal structures.…”

Section: Introductionmentioning

confidence: 99%

Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids

et al. 2021

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While ionic liquids have proved to be versatile materials for a wide spectrum of applications, e.g., energy, materials, and medicine, several challenges remain concerning the rational design of novel materials. In light of this, a series of four triphenylphosphonium-based ionic liquids have been synthesized for the first time. These compounds exhibit high thermal stability with decomposition temperatures up to 450 °C. Their solid-state structures are characterized by single-crystal X-ray diffraction and the intermolecular interactions rigorously analyzed via Hirshfeld surface analysis. It was found that the unique geometries of the anions used in the study form distinct interactions with the cations. The interactions in the crystalline state are correlated with the thermal properties of the four ionic liquids to rationalize the melting points and phase transitions for each compound. The observed arrangements of the alkyl chains on the cations are investigated computationally to gain an understanding of how rotational freedom may impact the thermal properties of the compounds. By intention, each IL reported in this work offers a unique property profile and contributes to the ever-growing ionic liquid catalog.

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Section: Introductionmentioning

confidence: 99%

Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids

et al. 2021

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“…A brief summary and rationalization are provided here, establishing context for the study. Full details can be found within the manuscripts. , …”

Section: Resultsmentioning

confidence: 99%

“…Specifically, alkyl−π interactions were theorized to be important NCIs for these cations. A follow-up study helped verify the formation and importance of π interactions wherein a significant percentage of π stacking interactions between the cation and anion were observed . Thus, for the present study, we examined how these π interactions can be altered through targeted modification of both the steric and electronic architecture of TPP ILs.…”

Section: Resultsmentioning

confidence: 99%

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Planting the Seeds of a Decision Tree for Ionic Liquids: Steric and Electronic Impacts on Melting Points of Triarylphosponium Ionic Liquids

Scheuren,

Teodoro,

Witters

et al. 2024

J. Phys. Chem. B

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While machine learning and artificial intelligence offer promising avenues in the computer-aided design of materials, the complexity of these computational techniques remains a barrier for scientists outside of the specific fields of study. Leveraging decision tree models, inspired by empirical methodologies, offers a pragmatic solution to the knowledge barrier presented by artificial intelligence (AI). Herein, we present a model allowing for the qualitative prediction of melting points of ionic liquids derived from the crystallographic analysis of a series of phosphonium-based ionic liquids. By carefully tailoring the steric and electronic properties of the cations within these salts, trends in the melting points are observed, pointing toward the critical importance of π interactions to forming the solid state. Quantification of the percentage of these π interactions using modern quantum crystallographic approaches reveals a linear trend in the relationship of C−Hπ and π−π stacking interactions with melting points. These structure−property relationships are further examined by using computational studies, helping to demonstrate the inverse relationship of dipole moments and melting points for ionic liquids. The results provide valuable insights into the features and relationships that are consistent with achieving low T m values in phosphonium salts, which were not apparent in earlier studies. The data gathered are presented in a simple decision tree format, allowing for visualization of the data and providing guidance toward developing yet unreported compounds.

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“…Due to its simple tunable, designer, non-toxic, non-flammable, and low volatility qualities, imidazolium-based ILs are usually considered a green solvent since they may be utilized for synthesis, catalysis, solar cell, and desulfurization of fuel applications in a variety of disciplines [16]. 1,2-azido alcohols were created utilizing a magnetic catalyst and dicationic ionic liquid at room temperature.…”

Section: Introductionmentioning

confidence: 99%

Material Synthesis, Spectral, Optical and Antimicrobial Activity of Imidazolium Based Aldehydic Ionic Liquids: 1–Ethyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium bromide (I) and 1-butyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium chloride (II)

Sudhalakshmi,

Rajathi

2023

J. Sci. Res.

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We successfully produced imidazolium aldehydes from imidazolium alcohols for the first time using copper wire and no oxidizing agents. The findings of IR, UV, 1H-NMR, and 13C-NMR spectral examinations all indicated complete Oxidation of the alcohols, which was further demonstrated by those findings. The oxidation technique was used to create the ionic liquids 1-ethyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium; bromide and 1-butyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium; chloride. Using elemental and spectral analyses confirmed the structure of the synthesized compounds (I) and (II). FT-IR analysis was used to determine the presence of functional groups in the grown samples (I) and (II), and 1H-NMR and 13C-NMR spectral analysis were performed to confirm the environment of the elements (C, H). A UV-Visible-NIR spectrophotometer was implemented to determine the optical absorption value for samples (I) and (II). Using DSC analysis, the thermal stability and decomposition were seen. Bacillus Cereus, Staphylococcus Aureus, Enterobacter Coacae, and Staphylococcus Haemolytics were used in an antimicrobial study for samples (I) and (II), and the results are compared with control Ciprofloxacin.

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Examining the interactions of a thermally robust task-specific phosphonium-based ionic compound

Cited by 4 publications

References 60 publications

Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids

Developing Structural First Principles for Alkylated Triphenylphosphonium-Based Ionic Liquids

Planting the Seeds of a Decision Tree for Ionic Liquids: Steric and Electronic Impacts on Melting Points of Triarylphosponium Ionic Liquids

Material Synthesis, Spectral, Optical and Antimicrobial Activity of Imidazolium Based Aldehydic Ionic Liquids: 1–Ethyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium bromide (I) and 1-butyl-3-methyl-2-(2-oxo-ethyl)-3H-imidazol-1-ium chloride (II)

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