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Ionic liquids
JOURNAL OF MOLECULAR LIQUIDS · 2025 · IF 5.2

Nanoarchitectonics with designed sulfur-based functionalized azobenzene ionic liquids for low-temperature UV light switching systems

Jiahao Song,Hao Wu,Kaihu Zhang,Ruirui Liu,Yunfan Yang,Xinyue Zhang,Ahmed Elsherif,Ning Ma,Alaa S. Abd-El-Aziz

Ionic liquids (ILs) have been widely used as flexible sensors due to their tunable properties, low vapor pressure, and high electrical conductivity. ILs containing sulfonium cations have exhibited low melting points, high conductivity, and excellent stability comparable to imidazolium-based ILs, rendering them promising candidates for low-temperature sensing applications. Nevertheless, the unique properties of functionalized sulfonium-based ILs pose challenges for their synthesis using conventional methods, thereby limiting their widespread utilization. In this study, we propose an efficient approach for the preparation of functionalized sulfonium-based ILs and, for the first time, obtain ILs capable of ultraviolet (UV) light sensing at −10 °C. The synthesized ILs maintain their liquid state over a broad temperature range (−30 °C to 150 °C) and exhibit sensitive responses to UV light under complex environments, including low and high temperatures, as well as underwater, demonstrating great potential for their applications as flexible sensors.

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PETROLEUM CHEMISTRY · 2018 ·Vol. 58 ·期 1 ·56-61 · IF 0.932

Synthesis of raspberry ketone via Friedel-Crafts alkylation reaction catalyzed by sulfonic acid-functional ionic liquids

Wang Wang,He Zhenzhen,Li Conghao,You Zhixiang,Guo Hongyun

Phenol and butanolone catalyzed by different SO 3 H-functionalized ionic liquids (ILs) for synthesis of raspberry ketone (RK) had been investigated. The influences of different ionic liquids, reaction time, reaction temperature, reactant ratio, the amount of ionic liquid were investigated. The yield of raspberry ketone was 82.5% under the optimum reaction condition. In addition, the ILs (3-sulfo)propyltriamine bisulfate ([TEA-PS][HSO 4 ]) can be recycled up to five consecutive times without loss of activity. This method had the advantages of mild conditions, high product yield, easy to separate from the product, as well as environmentally friendly procedure. At the same time, the possible reaction mechanism was discussed.

CAS / MDL: 1633-83-6 121-44-8
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Advanced Energy Materials · 2024 · IF 24.4

Electric Double Layer Theory of Interfacial Ionic Liquids for Capturing Ion Hierarchical Aggregation and Anisotropic Dynamics

Qiang Wang,Zhiguo Qu,Di Tian

Compared to aqueous ions, ionic liquids (ILs) consist entirely of cations and anions, and they function in energy conversion and storage owing to unique properties. Classical electric double layer (EDL) theory born a century ago gives essential insights into aqueous interfaces, whereas it fails in ILs due to overlooking ionic geometries and interactions, leaving a theoretical gap in describing IL interfaces. This study captures IL fingerprints by combining nuclear magnetic resonance experiments, quantum chemistry investigations, and first-principles molecular simulations. Based on these findings, an EDL theory is proposed to reflect hierarchical aggregation structure and anisotropic dynamics for interfacial ILs. It involves four elements including ion geometries, ion–ion interactions, ion–wall interactions, and temperature and interfacial electric field effects. Specifically, polyatomic ions with nonuniform shapes are cornerstones for successive elements. Cation–anion non-oxygen hydrogen bonds and cation–cation π + –π + stacking generate bound clusters. Ion–wall adsorption causes hierarchical aggregation patterns, and cation–wall parallel stacking creates anisotropic dynamics at interfaces. Moreover, the thermal-weakened ionic interactions and electric field-enhanced interfacial electron transfer alter the aggregation states and dynamic properties of interfacial ILs. This theory is adaptable to various IL–wall combinations, advancing electrolyte design for next-generation electrochemical energy devices.

CAS / MDL: 143314-16-3
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

Amino acid-based ionic liquids as water-ethylene glycol additives towards superior lubricity and corrosion resistance

Xuemin Sun,Xiao Liu,Qiang Chen,Pingxia Guo,Yanyan Bai,Kun Zou,Ming Yi,Shuyan Yang,Meirong Cai,Feng Zhou,Weimin Liu

Two novel amino acid-based ionic liquids (AAILs) were synthesized and their tribological properties as water-ethylene glycol (W-EG) lubricant additives were investigated. The addition of 1 wt% of both AAILs to W-EG can significantly enhance the anti-corrosion, friction-reducing and anti-wear properties of the lubricants. Compared to W-EG, the coefficient of friction and wear volume are reduced by about 50% and 75%, respectively. The physical adsorption film and the tribochemical reaction film derived from AAILs collectively establish a protective barrier at the friction interface, endowing the lubricants with superior lubricity and load-carrying capacity. These two sulfur-free and halogen-free AAILs are promising for application in metal working fluids and hydraulic fluids.

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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2012 · IF 2.237

Selective Extraction of 1-Hexene Against n-Hexane in Ionic Liquids with or without Silver Salt

Rulong Li,Huabin Xing,Qiwei Yang,Xu Zhao,Baogen Su,Zongbi Bao,Yiwen Yang,Qilong Ren

This paper presents an extensive study on the feasibility of ionic liquids (ILs) for the extractive separation of a 1-hexene/n-hexane mixture. Seventeen ILs were tested at 313 K. The extraction selectivities of 1-hexene to n-hexane were in the range 1.5–3.0. The chemical structures of anion and cation in ILs greatly affected the extraction, and the functional groups, such as carbon–carbon double bond, nitrile, ester, and amide, in the ILs led to higher selectivities. The increase of alkyl chain length in cation led to the increase of extraction capacity of 1-hexene. To increase the distribution of 1-hexene in IL phase, silver salt was added to the ILs. It was found that ILs containing silver salt had a high distribution of 1-hexene, as well as high selectivity of 1-hexene against n-hexane. The extraction efficiency increased with the concentration of silver salt in ILs. When the initial feed concentration of 1-hexene was smaller, the selectivity of 1-hexene to n-hexane was higher. A simple mathematical model has been developed to describe the total 1-hexene content in the reaction media under study, on the basis of the formation of complexes between silver and 1-hexene with different stoichiometry. This work proves that the ILs can act as effective extractants in 1-hexene/n-hexane separation.

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TALANTA · 2012 · IF 3.794

Ionic liquids with amino acids as cations: Novel chiral ligands in chiral ligand-exchange capillary electrophoresis

Xiaoyu Mu,Li Qi,Haizhi Zhang,Ying Shen,Juan Qiao,Huimin Ma

Ionic liquids (ILs) with l -proline ( l -Pro) as cations have been developed for the novel chiral ligands coordinated with Cu(II) in chiral ligand exchange capillary electrophoresis (CLE-CE). Four kinds of amino acid ionic liquids (AAILs), including [ l -Pro][CF 3 COO], [ l -Pro][NO 3 ], [ l -Pro][BF 4 ] and [ l -Pro 2 ][SO 4 ], were successfully synthesized. Among them, [ l -Pro][CF 3 COO] was selected as the model ligand to optimize the separation conditions. The influences of AAIL concentration, pH, and methanol concentration on efficiency of chiral separation were investigated. Then it has been testified that the optimal buffer solution consisted of 25.0   mM Cu(Ac) 2 , 50.0   mM AAIL and 20% (v/v) methanol at pH 4.0. The interesting thing is well enantioresolution could be observed with [ l -Pro][CF 3 COO] as the new chiral ligand and nine pairs of labeled d , l -AAs were successfully separated with the resolution ranging from 0.93 to 6.72. Meanwhile, the baseline separation of labeled d , l -AAs could be achieved with the other three kinds of AAILs as ligands. The results have demonstrated the good applicability of AAILs with AAs as cations for chiral separation in CLE-CE system. In addition, comparative study was also conducted for exploring the mechanism of the AAILs as new ligands in CLE-CE.

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ELECTROANALYSIS · 2011 ·Vol. 23 ·期 12 ·2870-2877 · IF 2.721

Electrochemical Quantification of Hygroscopicity of Ionic Liquids with Solution-Dissolved Potassium Ferricyanide as the Redox Probe

Qin Qian,Ping Yu,Hanjun Cheng,Xiang Wang,Lifen Yang,Lanqun Mao

Quantification of hygroscopicity of ionic liquids (ILs) is of great importance in both fundamental studies and practical applications of ILs. This study demonstrates an electrochemical method for effectively quantifying the hygroscopicity of ILs through electrochemically monitoring water contents absorbed into ILs. The measurements of water content absorbed into the ILs are performed with square wave voltammetry (SWV) based on the water-induced enhancement of diffusion of solution-dissolved potassium ferricyanide (K 3 Fe(CN) 6 ) redox probe. For demonstration, two kinds of ILs with different hygroscopicity (i.e., hydrophilic Bmim + Gly − and hydrophobic Bmim + PF 6 − ) are employed in this study. The dissolution of K 3 Fe(CN) 6 redox probe into ILs is found to have little effect on the hygroscopicity of ILs. The hygroscopicity of ILs is thus able to be quantified by monitoring water content absorbed into ILs as a function of time when ILs are stored at room temperature and standard atmospheric pressure under 55 % relative humidity (RH). Under the conditions employed in this study, the hygroscopicity of Bmim + Gly − and Bmim + PF 6 − is determined to be 1.33 M per hour and 0.05 M per hour, respectively, which are almost consistent with those measured with Karl Fischer titration under the same conditions. The electrochemical method demonstrated in this study is experimentally simply and environmentally benign and may be potentially extended for general quantification of hygroscopicity of ILs.

CAS / MDL: 616-47-7 17084-13-8
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Aqueous solutions of sterically hindered amino acid ionic liquids for rapid and efficient capture of CO2

Hangzhi Wu,Shuyue Wen,Xiaomin Zhang,Shule Zhang,Xuefeng Guo,Youting Wu

Sterically hindered amines (SHAs), such as 2-amino-2-methyl-1-propanol (AMP), are an important subclass of conventional absorbents with large CO 2 capacity, while ionic liquids (ILs) are novel materials with unique physiochemical properties including negligible vapor pressure and high thermal stability. To combine the characteristics of these two kinds of CO 2 absorbents together, we proposed and successfully synthesized a series of new sterically hindered amino acid ionic liquids (SHAAILs). These SHAAILs (aqueous solutions) were proved to have excellent physiochemical properties, large CO 2 capacity (up to 0.92 mol mol −1 at 313.2 K, 1.0 bar), and fast absorption rate (greater than AMP). Dynamic absorption and thermal regeneration experiments were done to further illustrate the capability of SHAAILs in absorbing and desorbing CO 2 , and [N 1111 ][β-iPrNH-Ala] was found to be an excellent CO 2 absorbent owing to its suitable steric hinderance and also its ionic nature. NMR analysis confirms that the SHAAILs of suitable steric hinderance undergo the carbamate-mediated rapid hydrolysis mechanism in absorbing CO 2 . Due to the comprehensive advantages of SHAAILs, they are believed to have great potentials as efficient CO 2 absorbents in practical applications.

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APPLIED CATALYSIS A-GENERAL · 2017 · IF 4.339

Dialkylpyrazolium ionic liquids as novel catalyst for efficient fixation of CO2 with metal- and solvent-free

Yuan Ma,Ci Chen,Tengfei Wang,Jingshun Zhang,JiaJia Wu,Xiangdong Liu,Tiegang Ren,Li Wang,Jinglai Zhang

The efficient fixation of CO 2 without co-catalyst and solvent under metal-free condition is still an urgent topic in sustainable chemistry. In this work, a series of dialkylpyrazolium ionic liquids are employed to promote the cycloaddition of CO 2 and PO to produce PC. They would be easily synthesized by a simple one-pot reaction. The effect of alkyl chain length in cation and different anion is explored. Diethylpyrazolium iodide presents the excellent catalytic activity with the product yield of 96% and selectivity of 99% in a benign condition. Moreover, the catalyst could be reused for at least five times without significant loss of catalytic activity. An intensive structure-activity research testifies that the cycloaddition of CO 2 with PO is activated by a synergistic effect from both cation and anion of ILs. To confirm it, the detailed mechanism is investigated by density functional theory associated with the non-covalent interactions and atoms in molecule analysis. Besides the electrostatic interaction between cation of ionic liquid and PO, the noncovalent interaction, especially for hydrogen bond, plays a vital role in promoting the reaction.

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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2024 · IF 4.9

Phase diagrams and formulation mechanism of microemulsions with hydroxyl group functional anionic surface active ionic liquids

Ruping Huang,Jingchun Zhang,Qiqi Wang,Haoyuan Chen,Yiyue Shen,Yupei Deng,Guowei Wang,Linghua Zhuang

One functional hydroxyl group-containing anionic surface active ionic liquids (SAILs), 1-(3-hydroxypropyl)-3-methylimidazolium dodecyl sulfate ([MPmim][DS]) and 1-(3-hydroxypropyl)-3-butylimidazolium dodecyl sulfate ([MPbim][DS]) were synthesized and characterized with 1 HNMR, 13 CNMR, FT-IR spectroscopy, thermogravimetric analysis (TGA), and elemental analysis . The critical micellar concentration (CMC) values of [MPmim][DS] and [MPbim][DS] were obtained through measurements of surface tension and electrical conductivity . The capability of [MPmim][DS] and [MPbim][DS] to form microemulsions was assessed. The influence of the hydroxyl group of imidazolium cation on microemulsion formulation was elucidated using Density functional theory (DFT) simulations. Critical micellar concentration (CMC) values for [MPbim][DS] and [MPmim][DS] are 0.51 mmol/L and 0.99 mmol/L, respectively. The micellization processes of [MPbim][DS] and [MPmim][DS] are spontaneous, endothermic, and entropy-driven. [MPmim][DS] or [MPbim][DS] as surfactant , ethyl laurate microemulsions are formulated. The single-phase region area (S ME ) percent of ethyl laurate microemulsions are 60% and 66%. The single-phase region area percent of different microemulsions follows the trend: [MPbim][DS] > [MPmim][DS]. Introducing the functional hydroxyl group into the imidazolium cation significantly expands the S ME area of microemulsions. DFT simulations are employed to analyze hydrogen bonding and electronic energy interactions among cations, DS anion, [MPmim][DS], [MPbim][DS], and ethyl laurate. Two types of hydrogen bonds are formed in [MPmim][DS] or [MPbim][DS], as C-H…O, and O-H…O. In [MPmim][DS], the hydroxyl group of imidazolium cation participates in the formation of a strong hydrogen bond with DS anion, exemplified by strong hydrogen bond O18-H19…O64 (1.972 Å). These advancements offer critical insights into the design of surface active ionic liquids , enhancing their functional properties and broadening the potential for innovative microemulsion applications in various industries.

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ACS Applied Materials & Interfaces · 2024 · IF 8.3

Preparation of Antibacterial Biobased Fibers by Triaxial Microfluidic Spinning Technology Using Ionic Liquids as the Solvents

Zhimin Zhao,Junlei Wang,Hanmeng Yuan,Jie Xu,Hongshuai Gao,Yi Nie

Bacterial infections have become a serious threat to public health. The utilization of antibacterial textiles offers an effective way to combat bacterial infections at the source, instead of relying solely on antibiotic consumption. Herein, efficient and durable antibacterial fibers based on quercetin and cellulose were prepared by a triaxial microfluidic spinning technology using ionic liquids (ILs) as the solvents. It was indicated that the structure and properties of the antibacterial fibers were affected by the type of IL and the flow rates during the triaxial microfluidic spinning process. Quercetin regenerated from [Emim]Ac underwent structural transformation and obtained an increased water solubility, while quercetin regenerated from [Emim]DEP remained unchanged, which was proven by FI-IR, XRD, and UV analyses. Furthermore, antibacterial fibers regenerated from [Emim]Ac exhibited the highest antibacterial activity of 96.9% against S. aureus, achieved by reducing the inner-to-outer flow rate ratio to 0 and concentrating quercetin at the center of fibers. On the other hand, when [Emim]DEP was used as the solvent, balancing the inner-to-outer flow rate ratio to concentrate quercetin in the middle layer of the fiber was optimal for achieving the best antibacterial activity of 93.3% because it promised both the higher encapsulation efficiency and release rate. Computational fluid dynamics (CFD) mathematically predicted the solvent exchange process during triaxial spinning, explaining the influence of IL types and flow rates on quercetin distribution and encapsulation efficiency. It was indicated that optimizing the distribution of antibacterial agents within the fibers can fully unleash its antibacterial potential while preserving the mechanical properties of the fiber. Therefore, the proposed simple triaxial spinning strategy provides valuable insights into the design of biomedical materials.

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TRIBOLOGY INTERNATIONAL · 2024 · IF 6.1

Synergistic adaptive system involving protic ionic liquids and copper nanoparticles for eco-friendly water-based lubrication

Diange Guo,Keying Hua,Lehao Zhao,Hongxiang Yu,Feng Zhou,Xiaobo Wang,Xia Zhang

As environmental awareness continues to rise, research on water-based protic ionic liquids (PILs) and nanoparticle (NP) additives has become crucial in the field of green lubrication. This study designed two water-based PILs with different alkyl chain lengths and synthesized copper nanoparticles for their combination. The tribological tests showed that the synthesized PILs exhibited excellent friction-reducing and anti-wear properties. When PILs were combined with copper nanoparticles, the friction coefficient was further reduced by up to 85 %. The tribological performance was influenced by the structure of the alkyl chains. The combination of long chains PIL with copper nanoparticles showed a more pronounced effect, reducing the wear rate to 0.013 and achieving ultra-low friction. Through particle size and zeta potential analysis, we found that the dispersion stability of copper nanoparticles was significantly improved, with no significant aggregates forming even after 60 days of storage. This effectively addressed the agglomeration and sedimentation issues of nanoparticles, extending their lifespan as lubricant additives. This study confirms the synergistic optimization between PILs and copper nanoparticles, providing new insights into the use of nanoparticles as additives in water-based lubricants and expanding their potential applications in the lubrication field.

CAS / MDL: 25322-68-3
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