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GREEN CHEMISTRY · 2024 · IF 9.3

Biocompatible diimidazolium based ionic liquid systems for enhancing the solubility of paclitaxel

Yanhui Hu,Hua Yue,Shiqi Huang,Bingxi Song,Yuyuan Xing,Minmin Liu,Gongying Wang,Yanyan Diao,Suojiang Zhang

Paclitaxel (PTX) is a crucial medication employed in the treatment of various cancers, and its limited solubility has been a persistent clinical hurdle. Ionic liquids (ILs), considered as “green solvents”, possess remarkable attributes such as exceptional miscibility, tailorable properties, and versatility. These properties have ushered in a revolution in the realm of biomedicine, particularly in addressing the solubility challenges of poorly soluble drugs. In this work, low-toxicity diimidazolium based ILs were introduced into a PTX dissolution system for the first time. Compared to mono-imidazolium based ILs, diimidazolium based ILs exhibited lower in vitro cytotoxicity and the substitution of Cremophor EL (CrEL) with biocompatible [C10(MIM)2][Br]2 and water resulted in lower cytotoxicity at a certain concentration. Furthermore, [C10(MIM)2][Br]2 could effectively improve the solubility of PTX, and this enhancement was strongly correlated with the length of the carbon chain in the cation and the IL concentration. Significantly, the [C10(MIM)2][Br]2-based dissolution system demonstrated the capability to attain a PTX content that is on par with the widely used commercial drug Taxol. Besides, the [C10(MIM)2][Br]2–PTX complex displayed excellent physical stability for a long period of time, with no significant change of PTX concentration in the solution. Additionally, various interactions existed between [C10(MIM)2][Br]2 and PTX, encompassing hydrophobic interactions, π–π stacking, CH–π interactions, and hydrogen bonds. The results indicated that the diimidazolium based IL system showed promise as a biocompatible platform for the delivery of PTX.

研究领域: 药学 · 生物医学工程
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Gels · 2022 ·Vol. 8 ·期 1 ·52 · IF 4.432

Fast Gelation of Poly(ionic liquid)-Based Injectable Antibacterial Hydrogels

Che Zhao,Chengju Sheng,Chao Zhou

Traditional antibacterial hydrogels have a broad-spectrum bactericidal effect and are widely used as wound dressings. However, the biological toxicity and drug resistance of these antibacterial hydrogels cannot meet the requirements of long-term clinical application. Imidazolium poly(ionic liquids) (PILs) are polymeric antibacterial agents exhibiting strong antibacterial properties, as they contain a strong positive charge. In this study, two imidazolium PILs, namely poly(N-butylimidazolium propiolic acid sodium) (PBP) and poly(N-(3,6-dioxaoctane) imidazolium propiolic acid sodium) (PDP), as high efficiency antibacterial agents, were synthesized by polycondensation reaction. Then, the PILs were compounded with polyethylene glycol (PEG) by a thiol-yne click reaction to prepare injectable antibacterial hydrogels. An in vitro assay showed that the injectable antibacterial hydrogels could not only quickly killEscherichia coli(E. coli) andStaphylococcus aureus(S. aureus), but also had low toxicity for human skin fibroblasts cells (HSFs) and human umbilical vein endothelial cells (HUVECs), respectively. Additionally, the lipopolysaccharide (LPS) inflammation model revealed that the injectable antibacterial hydrogels also had anti-inflammatory effects, which would be advantageous to accelerate wound healing.Keywords:antibacterial agents;imidazolium poly(ionic liquids);injectable hydrogels;anti-inflammatory

研究领域: 材料科学 · 生物医学工程 · 药剂学
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JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY · 2020 ·Vol. 146 ·期 3 ·1063-1076 · IF 2.731

Preparation and curing kinetics of intrinsic flame retardant epoxy resin system based on polyoxometalates

Jiao Enxiang,Wu Kun,Qu Zhencai,Liu Yingchun,Lu Maoping,Nan Bingfei,Chen Weilong,Liang Liyan

In this work, phosphomolybdic acid (PMoA) was used as a kind of eco-friendly flame retardant precursor. Then, a green intrinsic flame retardant was successfully prepared by chemically modifying PMoA with imidazolium (IM), which can be well dispersed in epoxy matrix without using any solvent. DSC results demonstrated that IM-PMoA can chemically react with epoxy monomer under heating with a moderate heat release, which greatly reduced the migration resistance of PMoA in water (1.2871% vs. 0.0439%). Meanwhile, curing kinetics indicates EP/IM-PMoA composites have higher activation energy (98.06 kJ mol −1 ) than pure EP (75.48 kJ mol −1 ). Besides, epoxy composite can pass V-0 rating with 8 mass% IM-PMoA addition. Compared to pure epoxy, the obvious decrease in the values of peak heat release rate and total smoke release were 37.78% and 31.03%, respectively. In addition, Raman spectrum indicated that the residual carbon is highly graphitized, which may be attributed to the superb catalytic carbonation ability of PMoA. The high-quality char layer can be used as physical barrier for inhibiting the heat diffusion and degradant transfer. As a result, excellent flame retardant and smoke suppression properties were achieved. This work provides a new idea to prepare a green intrinsic flame retardant for epoxy based on imidazolium.

CAS / MDL: 85100-77-2 931-36-2
研究领域: 材料科学 · 化学工程
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JOURNAL OF APPLIED POLYMER SCIENCE · 2025 · IF 2.8

Curing Mechanism and Properties Epoxy Resins With Main-Chain Polyimidazolium Ionic Liquids

Jingshi Liang,Bo Liu,Ye Wang,Delai Jiao,Xiaolin Shi,Zhiming Pan,Chunling Zhang

Ionic liquids have aroused considerable attention in the fields of polymer and materials science due to their designability and distinctive qualities. Epoxy resin (EP) with antimicrobial and stain-resistant properties is important for the service life of the material and for eliminating potential health hazards. In this study, a series of main-chain polyimidazolium ionic liquids (PIMILs) differing in the alkyl chain length of cation sizes (propyl, butyl, hexyl, octyl, decyl, dodecyl, 3,6-dioxaoctyl, and 4,7,10-trioxatridecyl) were synthesized by the Debus–Radziszewski reaction, and used as curing agents for EPs. The results of the curing conditions of their corresponding EPs revealed the regularity in the curing conditions dependent mainly on alkyl chain length. Meanwhile, the influence of the chloride anion and cation size on thermal stability, the glass transition temperature ( T g ), and thermomechanical properties of the epoxy composites were discussed, Finally, the water contact angles of thermosets ranged from 78.1° to 104.5°, and the thermosets could effectively kill multiple strains of bacteria and remove the biofilm.

研究领域: 材料科学 · 高分子化学
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Polymers · 2020 ·Vol. 12 ·期 2 ·370 · IF 3.426

Poly(ionic liquid)-Modified Metal Organic Framework for Carbon Dioxide Adsorption

Guangyuan Yang,Jialin Yu,Sanwen Peng,Kuang Sheng,Haining Zhang

The design and synthesis of solid sorbents for effective carbon dioxide adsorption are essential for practical applications regarding carbon emissions. Herein, we report the synthesis of composite materials consisting of amine-functionalized imidazolium-type poly(ionic liquid) (PIL) and metal organic frameworks (MOFs) through complexation of amino groups and metal ions. The carbon dioxide adsorption behavior of the synthesized composite materials was evaluated using the temperature-programmed desorption (TPD) technique. Benefiting from the large surface area of metal organic frameworks and high carbon dioxide diffusivity in ionic liquid moieties, the carbon dioxide adsorption capacity of the synthesized composite material reached 19.5 cm3·g−1, which is much higher than that of pristine metal organic frameworks (3.1 cm3·g−1) under carbon dioxide partial pressure of 0.2 bar at 25 °C. The results demonstrate that the combination of functionalized poly(ionic liquid) with metal organic frameworks can be a promising solid sorbent for carbon dioxide adsorption.Keywords:metal organic framework;poly(ionic liquid);carbon dioxide;adsorption;imidazolium;temperature-programmed desorption

研究领域: 材料科学 · 环境科学
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JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY · 2013 ·Vol. 51 ·期 9 ·1912-1923 · IF 3.543

Design, synthesis, and self-assembly manipulating of polymerized ionic liquids contained imidazolium based on “Jacketing” effect

Liang Weng,Jiao-Jiao Yan,He-Lou Xie,Guan-Qun Zhong,Si-Qi Zhu,Hai-Liang Zhang,Er-Qiang Chen

A series of novel polymerized ionic liquids (PILs) contained imidazolium, poly (2,5-bis{[6-(1-butyl-3′-imidazolium)hexyl] oxy carbonyl}styrene salts) (denoted as P1  X − , X − Br − , BF 4 − , PF 6 − and TFSI − ) were successfully synthesized via radical polymerization. The chemical structures of the monomers and their corresponding PILs were confirmed by 1 H NMR, 13 C NMR, and Fourier transform infrared spectroscopy. Thermogravimetric analysis results showed that these PILs had excellent thermal stability. The phase transitions and liquid-crystalline (LC) behaviors of these polymers were investigated by differential scanning calorimetry, polarized light microscopy (PLM), and wide-angle X-ray diffraction. The combined experimental results showed that all the PILs could form hexagonal columnar (ϕH) LC ordered structures because of the strong interaction between the anions and cations in the side groups except for P1  TFSI − . The conductivities of monomers and PILs were sketchily investigated, and monomers had higher conductivities than those of conprespoding PILs. For comparison, we have synthesized a polymer without counter-anion, but similar to the chemical structure of P1  X − , poly (2, 5-bis{[6-(4-butoxy-4′-oxy phenyl) hexyl] oxycarbonyl} styrene) (denoted as P2). In this case, phenyl took place of imidazolium of side chain, and LC ordered structure did not form. The comparison between P1  X − and P2 suggested that ion played an important role in the constructing of LC ordered structure. © 2013 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013

CAS / MDL: 90076-65-6
研究领域: 高分子化学 · 材料科学
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RSC Advances · 2016 ·Vol. 6 ·期 37 ·31336-31346 · IF 3.289

Imidazolium functionalized polysulfone electrolyte membranes with varied chain structures: a comparative study

Baoqiang Zhang,Lingdong Li,Gaohong He,Fangyuan Gai,Fengxiang Zhang

The alkaline electrolyte membrane (AEM) is one of the key materials for alkaline electrolyte membrane fuel cells. While most studies focus on AEM performance in relation to cation structure, ion exchange capacity (IEC) and membrane architecture (cross-linking, composite, microphase separation), herein we report that AEMs of varied backbone structures and comparable IEC show remarkably different conductivities and alkaline stability. In particular, the AEM of imidazolium functionalized, isopropylene-containing polysulfone exhibits higher conductivity, but lower swelling- and alkali tolerance than those without such a unit. To confirm and mitigate the backbone influence, we grafted the isopropylene-containing polysulfone with imidazolium functionalized side chains. The resulting grafted membrane shows conductivity of 64 mS cm−1 at 80 °C, which is higher than that of the un-grafted AEMs; its stability against water swelling and hydroxide attack is also improved. Our study provides a new understanding on the structure–property correlation of AEMs, and thus is beneficial for designing high-performance electrolyte membranes for an alkaline fuel cell.

研究领域: 材料科学 · 燃料电池研究
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Polymer-Plastics Technology and Materials · 2020 · IF 0

The effect of imidazolated PPO with different alkyl chains on its performance as a high temperature proton exchange membrane

Shanshan Wang,Qifeng Li,Fanghui Wang

Designed and synthesized a series of imidazolium-functionalized Poly (2, 6-dimethyl-1, 4-phenylene oxide) (Im-PPO) containing pendant imidazole groups, which were used to supply functional sites for acid–base interaction with the doping phosphoric acid. The imidazolium-functionalized Poly (2, 6-dimethyl-1, 4-phenylene oxide) membranes obtained by the solution-casting method were doped with phosphoric acid (PA). The PA content, swelling, and tensile strength of the different membranes doped with PA were measured. With the increase of the length of side chains on the imidazole groups, the membrane showed different properties. The proton conductivity at a level of 3.7 × 10−2 S/cm was achieved at 160°C by the MeIm-PPO imidazolium composite membrane.

研究领域: 材料科学 · 化学工程
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2015 · IF 2.037

Solubility of 3,3′-(Oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] Dihexafluorophosphate in Water, Methanol, Ethanol, Acetone, and Acetonitrile and Binary Mixtures (Water + DMF) from (283.00 to 323.00) K

Jia-rong Guo,Bin Xu,Yan Wang,Ling-hua Zhuang,Guo-wei Wang

3,3′-(Oxidi-2,1-ethanediyl)bis[1-methyl-imidazolium] dihexafluorophosphate ([C4O(mim)2][PF6]2) was synthesized and confirmed with 1H NMR and FT-IR. The thermal stability of [C4O(mim)2][PF6]2 was studied with differential scanning calorimetry and thermogravimetric analyses. Using the dynamic method, the solubility of [C4O(mim)2][PF6]2 in five different pure solvents (water, methanol, ethanol, acetone, and acetonitrile) and binary mixtures (water + DMF) was measured at the temperature range from (283.00 to 323.00 K) at atmospheric pressure. The solubility of [C4O(mim)2][PF6]2 in those selected solvents increased with increasing temperature and DMF contents, but the rate of solubility is different. The experimental data were correlated with the modified Apelblat equation. Also, the solubility of [C4O(mim)2][PF6]2 and [C6O2(mim)2][PF6]2 was been compared in the same solvent.

研究领域: 化学工程 · 材料科学
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JOURNAL OF MATERIALS SCIENCE · 2016 ·Vol. 52 ·期 5 ·2473-2483 · IF 2.302

Design and fabrication of imidazolium ion-immobilized electrospun polyurethane membranes with antibacterial activity

Zhu Lixia,Dai Jinyue,Chen Lai,Chen Jing,Na Haining,Zhu Jin

By covalently immobilizing imidazolium ion onto molecular chain, functional polyurethane (PU) is fabricated and thus an effective way is initiated to prepare electrospun membranes with antibacterial activity. In the experiment, PUs containing imidazolium ion side group (Bmim-PUs) are synthesized through a two-step polymerization process. It includes prepolymerization of isophorone diisocyanate (IPDI) with polyester glycol and chain extension polymerization using imidazolium-based ionic diol (Bmim-OH). Then, the obtained Bmim-PUs are electrospun into fibrous membranes with a diameter of ~640 nm. After a careful assessment, antibacterial activities of electrospun membranes against Gram-positive Staphylococcus aureus and Gram-negative Escherichia coli are clearly exhibited. The antibacterial efficiency of Bmim-PUs on both bacteria species improves by 60% in comparison with PU without imidazolium ion. This research suggests a simple but effective methodology to design and fabricate ultrafine fibrous membrane with significant antibacterial activity. Moreover, the obtained fibrous membranes have widely potential applications in protective textiles, filtration, and biomedical engineering.

研究领域: 材料科学 · 生物医学工程
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Journal of CO2 Utilization · 2021 · IF 7.132

Bifunctional poly(ionic liquid) catalyst with dual-active-center for CO2 conversion: Synergistic effect of triazine and imidazolium motifs

Xu Fang,Chengcheng Liu,Li Yang,Tie Yu,Dong Zhai,Wenling Zhao,Wei-qiao Deng

Developing heterogeneous catalyst containing both CO 2 -philic groups and catalytic active sites is highly desirable for efficient CO 2 chemical fixation. In this work, a triazine-functionalized poly(ionic liquid) (T-PIL) was designed and synthesized. This metal free catalyst showed extremely enhanced CO 2 adsorption and improved catalytic ability for the cycloaddition reaction of CO 2 without co-catalysts. Especially for the epoxides of large size and strong steric hindrance, the yields of the cyclic carbonates were improved up to three times in the presence of triazine motifs. An intramolecular synergistic mechanism of triazine and imidazolium motifs was proposed on the basis of density functional theory (DFT) calculations and diffused reflectance infrared Fourier transform spectroscopy (DRIFTS). The imidazolium groups with paired bromine anions acted as catalytic active sites and would enhance CO 2 activation and the ring-opening of epoxides. While the triazine groups acting as CO 2 -philic groups could enhance the CO 2 adsorption and activation. This work highlights that the incorporation of two motifs with synergistic effect in one catalyst can significantly improve its catalytic performance.

CAS / MDL: 96-09-3
研究领域: 催化化学 · 材料科学
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TALANTA · 2019 · IF 4.916

Imidazolium ionic liquids-derived carbon dots-modified silica stationary phase for hydrophilic interaction chromatography

Lijun Song,Haijuan Zhang,Jia Chen,Zhan Li,Ming Guan,Hongdeng Qiu

In this study, imidazolium ionic liquids-derived carbon dots (ImCDs) were successfully synthesized and bonded on the surface of spherical porous silica as a new stationary phase (Sil-ImCDs) for hydrophilic interaction chromatography (HILIC). First, the ImCDs were synthesized by the reaction of amino ionic liquids with citric acid , and then they were grafted onto the surface of aminopropyl-modified silica. A series of characterizations including infrared spectra, elemental analysis and laser confocal microscope proved that the preparation was successful. It was found that the Sil-ImCDs had good separation efficiency in the separation of bases, nucleosides , amino acids , saccharides and ginsenosides . It is interesting that we found that Sil-ImCDs has better hydrophilic chromatographic performance compared with methylimidazole-modified silica and aminopropyl-modified silica. It may be due to the rich functional group which is available after the formation of carbon dots from imidazolium ionic liquids and citric acid.

研究领域: 化學 · 分析科學
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