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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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POLYMER DEGRADATION AND STABILITY · 2024 · IF 6.3

Liquid phosphorus-based bis-imidazole compounds as latent curing agents for enhancing thermal, mechanical, and flame-retardant performances of single-component epoxy resins

Jingsheng Wang,Jun Wang,Fengyi Wang,Shuang Yang,Chaoqun Wu,Xi Chen,Kaiwen Chen,Pingan Song,Hao Wang,Siqi Huo

The escalating need for advanced, fire-resistant, single-component epoxy resin (EP) is fueled by its practicality and economic benefits, highlighting the necessity for the development of multifunctional flame-retardant latent curing agents. Herein, two liquid phosphorus-containing bis-imidazole compounds, PPDM and DPCMI, were synthesized as latent curing agents for EP, demonstrating multiple effects in improving latency, thermal stability, mechanical properties, and fire safety. EP/PPDM and EP/DPCMI showcased superior storage stability and rapid curing at moderate temperatures, with EP/PPDM standing out for its long shelf life of 7 d and being gelled within 18 min at 100 °C. The resulting thermosets presented increased glass transition temperatures (189.5 and 178.9 °C), due to the enhanced crosslinking densities. The presence of bis-imidazole groups in PPDM and DPCMI enabled EPs to form denser crosslinked networks, leading to improved mechanical strength and toughness. The limiting oxygen index (LOI) values of EP/PPDM and EP/DPCMI reached 29.5% and 29.0%, respectively. Compared to the control EP, EP/PPDM and EP/DPCMI showed 23.1% and 18.8% reductions in total heat release and 22.0% and 23.11% decreases in total smoke production. These results confirm the enhanced flame retardancy and smoke suppression of EP/PPDM and EP/DPCMI because of introducing phosphorus-containing groups. Even though the curing time was halved to 2.5 hours, EP/PPDM systems maintained satisfactory overall performances. Therefore, this work offers a scalable strategy for the fabrication of single-component EP systems combining rapid curing, satisfactory flame retardancy, and enhanced thermal stability and mechanical properties, aligning with the needs of industrial applications.

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 THERMAL ANALYSIS AND CALORIMETRY · 2018 ·Vol. 135 ·期 6 ·3005-3013 · IF 2.209

Preparation and characterization of nitrogen-rich bis-1-methylimidazole1H,1′H-5,5′-bistetrazole-1,1′-diolate energetic salt

Luo Liqiong,Jin Bo,Peng Rufang,Shang Yu,Xiao Lipengcheng,Chu Shijin

A new nitrogen-rich energetic salt of bis-1-methylimidazole 1 H ,1′ H -5,5′-bistetrazole-1,1′-diolate salt, (1- M ) 2 BTO, was synthesized and characterized (FT-IR, 1 H NMR, 13 C NMR, elemental analysis, and X-ray single-crystal diffraction). Results indicated that (1- M ) 2 BTO crystallizes in the triclinic space group P -1. The thermal decomposition behavior of (1- M ) 2 BTO was determined by differential scanning calorimetry (DSC) and thermogravimetric tandem infrared spectroscopy. The decomposition peak temperature of (1- M ) 2 BTO was 530 K, which suggested that the salt is strong heat resistance. The apparent activation energies were 130.56 kJ mol −1 (Kissinger’s method) and 132.50 kJ mol −1 (Ozawa’s method), respectively. The enthalpy of formation for the salt was calculated as 917.3 kJ mol −1 . The detonation velocity and detonation pressure of (1- M ) 2 BTO were 7448 m s −1 and 20.7 GPa, respectively, using the Kamlet-Jacobs equation. Furthermore, the sensitivity test results showed that its impact sensitivity is greater than 50 J and friction sensitivity is 180 N, indicating that it has a lower sensitivity.

研究领域: 化学 · 材料科学
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APPLIED ORGANOMETALLIC CHEMISTRY · 2024 ·Vol. 39 ·期 1 ·e7935 · IF 3.7

Polyethylene Glycol–Bridged Diimidazolium Polyoxometalates: Thermoregulated Reusable Catalysts for Selective Oxidation of Toluene to Benzaldehyde

Shu Qian,Fengli Yu,Yexin Luo,Bing Yuan,Congxia Xie,Shitao Yu

The oxidation of toluene to benzaldehyde holds great industrial significance, and it typically involves toxic reagents and/or affords difficult-to-separate product mixtures. Herein, polyethylene glycol (PEG)–bridged diimidazolium polyoxometalates (POMs) with a Keggin-type tungstovanadophosphoric heteropolyacid anion and various PEG-functionalized diimidazolium cations were prepared and evaluated as catalysts for the eco-friendly oxidation of toluene using aqueous tert -butyl hydroperoxide in acetonitrile. The bridging of diimidazolium cations by PEG enabled the fine-tuning of heteropolyanion redox properties and increased catalyst reactivity and solubility in the reaction system. The best-performing POM exhibited thermoregulated phase-separation behavior, that is, it was fully soluble in the reaction medium at elevated temperatures and hardly soluble at room temperature. Further, it showed almost no performance deterioration after sevenfold reuse and achieved an acceptable toluene conversion (82%) and benzaldehyde selectivity (68%). Thus, our work enables the development of eco-friendly processes for the catalytic oxidation of industrially relevant hydrocarbon and thus facilitates the establishment of a more sustainable society.

CAS / MDL: 25322-68-3
研究领域: 化学工程 · 催化科学
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ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES · 2019 ·Vol. 74 ·期 3 ·261-265 · IF 0.961

Synthesis and structural characterization of two coordination polymers constructed by bis(4-(1H-imidazol-1-yl)phenyl)methanone and 5-(tert-butyl)isophthalate ligands

Gao-Feng Wang,Shu-Wen Sun,Wei-Bing Wang,Hong Sun,Shao-Fei Song

Two coordination polymers, {[Co(bipmo)(tbip)]·3H 2 O} n ( 1 ) and {[Cd(bipmo)(tbip)]·3H 2 O} n ( 2 ) (bipmo=bis(4-(1 H -imidazol-1-yl)phenyl)methanone, H 2 tbip=5- tert -butylisophthalic acid), were synthesized by solvothermal methods and structurally characterized by elemental analyses, infrared spectroscopy, and single-crystal X-ray diffraction. The results from single-crystal X-ray diffraction data indicate that the solid state structures of 1 and 2 consist of metal-aromatic carboxylate layers, which are pillared by weak interactions to generate a three-dimensional network. The topological structures of 1 and 2 are uninodal nets based on 3-connected nodes with the Schläfli symbol of {6 3 }.

研究领域: 无机化学 · 材料科学
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FUEL PROCESSING TECHNOLOGY · 2022 · IF 8.129

Upgrading of furfural to C10 furoin catalyzed by diimidazole ionic liquids

Kun Yuan,Huangxian Zhang,Qiao Sun,Xiaohua Zhang,Dan Hou,Jing Chen,Changxiang Liu,Jinzhu Chen,Wanming Xiong

Biomass-based platform compound furfural can be upgraded to C 10 furoin, which is significant to the development and utilization of biomass energy . In this work, a series of diimidazole ILs were applied to explore a feasible way for upgrading of furfural to furoin. The results showed that the catalytic performance of diimidazole ILs were affected by the solvent and the structure of the anion and cation . Furoin yield could increase from 14.8% to 45.0% with the extension of the side chain, and it could be greatly enhanced by the transformation of ethyl group into unsaturated vinyl group. Theoretical calculations revealed it was due to the higher absorption energy and shorter distance between the di (vinylimidazole) ILs and furfural. Furthermore, the anion of diimidazole ILs also displayed influence by affecting the acidity and the electron distribution on the imidazole ring. Finally, the optimized yields of 84.4%, 82.0% and 84.8% were obtained by optimizing the BV 4 , FV 4 and SV 4 catalytic systems , respectively. Mechanistic studies suggested that C-2 deprotonation was the key to the reaction, and both the σ hyperconjugation and π-π conjugation with the imidazole ring could facilitated the reaction. This work may provide some reference in upgrading biomass energy

研究领域: 化学工程 · 生物质能
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Journal of Material Cycles and Waste Management · 2024 ·Vol. 26 ·期 2 ·1119-1130 · IF 2.7

Preparation of degradable polycarbonate from low boiling point organic matter of waste electrolyte

Duan Yunlong,Guo Liying,Zhou Qiao,Wang Haonan,Zhang Linnan,Shi Fa-Nian

In this paper, aliphatic polycarbonate (APC) was successfully prepared from low-boiling organic matter and aliphatic diols in waste electrolyte by ester exchange reaction and polycondensation reaction, and the process conditions were optimized to investigate the effects of catalyst type and dosage, type of aliphatic diol raw material, transesterification temperature, polycondensation temperature, polycondensation time, and polycondensation vacuum degree on the yield and molecular weight of the product. The structure and properties of the product APC were tested using Fourier transform infrared spectrometer (FTIR), H nuclear magnetic resonance spectra ( 1 HNMR), differential scanning calorimetry (DSC), thermal gravity analysis (TG), gel permeation chromatography (GPC), and electronic universal testing machine were used to test the structure and properties of the product APC. The results showed that the lithium biimidazole catalyzed the best effect and the synthesized APC had the correct structure and great properties, including good thermal stability, mechanical properties, and degradation properties. The product was degraded under the action of enzyme for 12 days, and its degradation rate could reach more than 98%, meeting the use standard of degradable polycarbonate. It has a good application prospect. Graphical Abstract

研究领域: 材料科学 · 环境科学 · 化学工程
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Petroleum Science · 2022 · IF 4.757

Adsorption behavior and wettability alteration of bis-imidazolium salts on vermiculite: Experimental and theoretical studies

Fan Ding,Tao Shen,Shan-Shan Mao,Xin Jin,Mang-Lai Gao

For further understanding the wettability alteration induced by organic salts, series of bis -imidazolium salts (EBMI, TBMI, HBMI, OBMI and DBMI) were employed for investigating their adsorption behavior and wettability alteration on vermiculite (Vt) by experimental and theoretical studies. The characterization results indicated that all bis -imidazolium salts had been loaded on Vts. The adsorption results showed that EBMI, TBMI, HBMI, OBMI and DBMI on Vt reached equilibrium of 0.159, 0.156, 0.145, 0.114 and 0.084 mmol g −1 around 30 min at 25 °C, respectively, which were sensitive to ionic strength and pH. Langmuir, statistical physical modelling and pseudo-second-order models could be well fitted with the adsorption data, and thermodynamic parameters suggested that the adsorption processes of bis -imidazolium salts were endothermic and spontaneous, indicating that the resultant bis -imidazolium salts could be self-assembled onto Vt in the form of the monolayer. Results of molecular dynamic simulation showed that bis -imidazolium salts were adsorbed on Vt with the lying-flat configuration, and the electrostatic interaction acted as the main interaction mechanism, which were consistent with that obtained experimentally. Changes of wettability of Vt induced by bis -imidazolium salts were verified by capillary rise experiments. Interestingly, the wettability of organo-Vts varied with the spacer length and the order was as follows: EBMI-Vt < TBMI-Vt < HBMI-Vt < OBMI-Vt < DBMI-Vt, which could be explained by their arrangements, hydrophobicity as well as the interaction energies. The longer the spacers of bis -imidazolium salts, the greater the absolute values of the interaction energy, the less the adsorbed bis -imidazolium salts, while the more hydrophobic of organo-Vt. This work aimed at revealing the adsorption behavior, mechanism as well as effect of bis -imidazolium salts on wettability alteration of negatively charged mineral surface, providing some information for the selection of flooding agent for enhanced oil recovery and wettability modifier.

研究领域: 化学 · 材料科学 · 石油工程
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JOURNAL OF APPLIED POLYMER SCIENCE · 2017 ·Vol. 134 ·期 44 ·45491 · IF 1.86

Synergistic effects of dual imidazolium polyoxometalates on intumescent flame retardant polypropylene

Chengle Wang,Zhijing Wang,Juan Li

The role of dual imidazolium polyoxometalates (POMs) in the flame retardancy of polypropylene/intumescent flame retardant (PP/IFR) composites was studied. The results showed that the structures of dual imidazolium POMs have a great effect on the flame retardancy of PP composites. The dual imidazolium POMs based on an ethyl group (EMIPMA) obtain the best flame retardant efficiency. With 15.5 wt % IFR and 0.5 wt % EMIPMA, the PP composites reach a limiting oxygen index of 25.7 and the UL-94 V-0 standard. However, the dual imidazolium POMs containing a butyl (BMIPMA) or hexyl (HMIPMA) group cannot achieve the UL-94 V-0 standard at the same formulation. Dual imidazolium POMs not only promote the formation of good char, but also induce the formation of intumescent char with a hierarchical and microporous structure that helps to prevent gas and heat from transferring from the flame to the resin. Therefore, the flame retardancy of PP/IFR composites is improved. However, excessive combustible components produced by BMIPMA or HMIPMA deteriorate the flame retardancy of PP/IFR composites. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017 , 134 , 45491.

研究领域: 材料科学 · 化学工程
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MATERIALS CHEMISTRY AND PHYSICS · 2019 · IF 2.781

Structural and mechanical characteristics of silane-modified PIPD/basalt hybrid fiber-reinforced polybenzoxazine composites

Hamid Abdelhafid Ghouti,Abdeldjalil Zegaoui,Mehdi Derradji,Li-wu Zu,Wan-an Cai,Jun Wang,Abdul Qadeer Dayo,Wen-bin Liu

Typically, hybrid fibers reinforced composites have the potential to provide materials with excellent mechanical properties . However, cost-effective, lightweight, easily manufactured and high-performance materials are even more attractive for the market and the industry. In this work, newly designed hybrid poly-pyridobisimidazole (PIPD) and basalt fibers (BFs) reinforced polybenzoxazine composites were investigated. Initially, the fibers were chemically modified with silane GX-560 coupling agent. Afterwards, the hybrid combinations were included in the resin and cured. The Fourier transform infrared spectra showed the chemical bond that results when the silane is grafted. The X-ray photoelectron spectroscopy scan provided the fibers atomic content and showed that the silane content was effectively raised after treatment. The microhardness and impact properties were markedly improved, reaching the maximum value of 570 MPa and 18.44 kJ/m 2 , respectively, compared to the reference resin with 347 MPa and 1.6 kJ/m 2 . This was due to the high-performance PIPD and BFs inclusive of their good interfacial adhesion and scattering around the surface confirmed by the fibers’ pull-out void and the random dispersion seen in the scanning electron microscope images.

CAS / MDL: 64-17-5
研究领域: 材料科学 · 机械工程
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INORGANICA CHIMICA ACTA · 2025 · IF 3.2

A turn-off fluorescent chemical sensor based on Bis-imidazole structure for highly selective and accurate detection of Cu2+ in living cells

Lu Ren,Jing Wang,Xiangchun Meng,Chang Liu,Ziyi Liao,Dawei Zhang

A novel highly selective and sensitive bis-imidazole fluorescent chemical sensor, 2,6-bis(4,5-diphenyl-1 H -imidazol-2-yl)-4-methylphenol (BMP) was synthesized and utilized for spectral sensing of Cu 2+ . After the addition of Cu 2+ , the green fluorescence of BMP solution quickly quenched, and in the presence of multiple metal ions showed good anti-interference to Cu 2+ , the detection limit was 1.59 nM. Job's plot and 1 H NMR analysis confirm that there is a 2:1 cooperative pattern between BMP and Cu 2+ . DFT calculations at the B3LYP/LANL2DZ/6-311 g level of theory were conducted to explore possible theoretical explanations. The detection of Cu 2+ by this probe has good repeatability under the alternating action of Cu 2+ and EDTA. Test strips made of BMP were used for rapid “naked-eye”detection of Cu 2+ in aqueous medium. The probe was successfully used to monitor Cu 2+ in living cells and real water samples.

CAS / MDL: 7310-95-4 94-36-0
研究领域: 分析化学 · 生物医学工程 · 材料科学
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