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Keywords = solvent-free quaternization

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20 pages, 4314 KB  
Article
Facile Synthesis of Dual-Functional Cross-Linked Membranes with Contact-Killing Antimicrobial Properties and Humidity-Response
by Ioanna Tzoumani, Denisa Druvari, Miltiadis Evangelidis, Alexios Vlamis-Gardikas, Georgios Bokias and Joannis K. Kallitsis
Molecules 2024, 29(10), 2372; https://doi.org/10.3390/molecules29102372 - 17 May 2024
Cited by 3 | Viewed by 1674
Abstract
Poly(2-hydroxyethylmethacrylate-co-2-(dimethylamino)ethyl methacrylate), P(HEMA-co-DMAEMAx), copolymers were quaternized through the reaction of a part of (dimethylamino)ethyl moieties of DMAEMA units with 1-bromohexadecane. Antimicrobial coatings were further prepared through the cross-linking reaction between the remaining DMAEMA units of these copolymers and the epoxide ring of poly( [...] Read more.
Poly(2-hydroxyethylmethacrylate-co-2-(dimethylamino)ethyl methacrylate), P(HEMA-co-DMAEMAx), copolymers were quaternized through the reaction of a part of (dimethylamino)ethyl moieties of DMAEMA units with 1-bromohexadecane. Antimicrobial coatings were further prepared through the cross-linking reaction between the remaining DMAEMA units of these copolymers and the epoxide ring of poly(N,N-dimethylacrylamide-co-glycidyl methacrylate), P(DMAm-co-GMAx), copolymers. The combination of P(HEMA-co-DMAEMAx)/P(DMAm-co-GMAx) copolymers not only enabled control over quaternization and cross-linking for coating stabilization but also allowed the optimization of the processing routes towards a more facile cost-effective methodology and the use of environmentally friendly solvents like ethanol. Careful consideration was given to achieve the right content of quaternized units, qDMAEMA, to ensure antimicrobial efficacy through an appropriate amphiphilic balance and sufficient free DMAEMA groups to react with GMA for coating stabilization. Optimal synthesis conditions were achieved by membranes consisting of cross-linked P(HEMA78-co-DMAEMA9-co-qDMAEMA13)/P(DMAm-co-GMA42) membranes. The obtained membranes were multifunctional as they were self-standing and antimicrobial, while they demonstrated a distinct fast response to changes in humidity levels, widening the opportunities for the construction of “smart” antimicrobial actuators, such as non-contact antimicrobial switches. Full article
(This article belongs to the Section Materials Chemistry)
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13 pages, 3969 KB  
Article
Immobilization of Ionic Liquid on a Covalent Organic Framework for Effectively Catalyzing Cycloaddition of CO2 to Epoxides
by Qianqian Yan, Hao Liang, Shenglin Wang, Hui Hu, Xiaofang Su, Songtao Xiao, Huanjun Xu, Xuechao Jing, Fei Lu and Yanan Gao
Molecules 2022, 27(19), 6204; https://doi.org/10.3390/molecules27196204 - 21 Sep 2022
Cited by 20 | Viewed by 4066
Abstract
Transforming CO2 into value-added chemicals has been an important subject in recent years. The development of a novel heterogeneous catalyst for highly effective CO2 conversion still remains a great challenge. As an emerging class of porous organic polymers, covalent organic frameworks [...] Read more.
Transforming CO2 into value-added chemicals has been an important subject in recent years. The development of a novel heterogeneous catalyst for highly effective CO2 conversion still remains a great challenge. As an emerging class of porous organic polymers, covalent organic frameworks (COFs) have exhibited superior potential as catalysts for various chemical reactions, due to their unique structure and properties. In this study, a layered two-dimensional (2D) COF, IM4F-Py-COF, was prepared through a three-component condensation reaction. Benzimidazole moiety, as an ionic liquid precursor, was integrated onto the skeleton of the COF using a benzimidazole-containing building unit. Ionization of the benzimidazole framework was then achieved through quaternization with 1-bromobutane to produce an ionic liquid-immobilized COF, i.e., BMIM4F-Py-COF. The resulting ionic COF shows excellent catalytic activity in promoting the chemical fixation of CO2 via reaction with epoxides under solvent-free and co-catalyst-free conditions. High porosity, the one-dimensional (1D) open-channel structure of the COF and the high catalytic activity of ionic liquid may contribute to the excellent catalytic performance. Moreover, the COF catalyst could be reused at least five times without significant loss of its catalytic activity. Full article
(This article belongs to the Special Issue Porous Organic Materials: Design and Applications)
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12 pages, 2266 KB  
Article
Negatively Charged MOF-Based Composite Anion Exchange Membrane with High Cation Selectivity and Permeability
by Xiaohuan Li, Noor Ul Afsar, Xiaopeng Chen, Yifeng Wu, Yu Chen, Feng Shao, Jiaxian Song, Shuai Yao, Ru Xia, Jiasheng Qian, Bin Wu and Jibin Miao
Membranes 2022, 12(6), 601; https://doi.org/10.3390/membranes12060601 - 10 Jun 2022
Cited by 6 | Viewed by 3625
Abstract
Every metal and metallurgical industry is associated with the generation of wastewater, influencing the living and non-living environment, which is alarming to environmentalists. The strict regulations about the dismissal of acid and metal into the environment and the increasing emphasis on the recycling/reuse [...] Read more.
Every metal and metallurgical industry is associated with the generation of wastewater, influencing the living and non-living environment, which is alarming to environmentalists. The strict regulations about the dismissal of acid and metal into the environment and the increasing emphasis on the recycling/reuse of these effluents after proper remedy have focused the research community’s curiosity in developing distinctive approaches for the recovery of acid and metals from industrial wastewaters. This study reports the synthesis of UiO-66-(COOH)2 using dual ligand in water as a green solvent. Then, the prepared MOF nanoparticles were introduced into the DMAM quaternized QPPO matrix through a straightforward blending approach. Four defect-free UiO-66-(COOH)2/QPPO MMMs were prepared with four different MOF structures. The BET characterization of UiO-66-(COOH)2 nanoparticles with a highly crystalline structure and sub-nanometer pore size (~7 Å) was confirmed by XRD. Because of the introduction of MOF nanoparticles with an electrostatic interaction and pore size screening effect, a separation coefficient (SHCl/FeCl2) of 565 and UHCl of 0.0089 m·h−1 for U-C(60)/QPPO were perceived when the loading dosage of the MOF content was 10 wt%. The obtained results showed that the prepared defect-free MOF membrane has broad prospects in acid recovery applications. Full article
(This article belongs to the Special Issue Ion-Selective Separation Membrane)
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15 pages, 9827 KB  
Article
Hypercrosslinked Ionic Polymers with High Ionic Content for Efficient Conversion of Carbon Dioxide into Cyclic Carbonates
by Xu Liao, Baoyou Pei, Ruixun Ma, Lingzheng Kong, Xilin Gao, Jiao He, Xiaoyan Luo and Jinqing Lin
Catalysts 2022, 12(1), 62; https://doi.org/10.3390/catal12010062 - 6 Jan 2022
Cited by 24 | Viewed by 3968
Abstract
The effective conversion of carbon dioxide (CO2) into cyclic carbonates requires porous materials with high ionic content and large specific surface area. Herein, we developed a new systematic post-synthetic modification strategy for synthesizing imidazolium-based hypercrosslinked ionic polymers (HIPs) with high ionic [...] Read more.
The effective conversion of carbon dioxide (CO2) into cyclic carbonates requires porous materials with high ionic content and large specific surface area. Herein, we developed a new systematic post-synthetic modification strategy for synthesizing imidazolium-based hypercrosslinked ionic polymers (HIPs) with high ionic content (up to 2.1 mmol g−1) and large specific surface area (385 m2 g−1) from porous hypercrosslinked polymers (HCPs) through addition reaction and quaternization. The obtained HIPs were efficient in CO2 capture and conversion. Under the synergistic effect of high ionic content, large specific surface area, and plentiful micro/mesoporosity, the metal-free catalyst [HCP-CH2-Im][Cl]-1 exhibited quantitative selectivities, high catalytic yields, and good substrate compatibility for the conversion of CO2 into cyclic carbonates at atmospheric pressure (0.1 MPa) in a shorter reaction time in the absence of cocatalysts, solvents, and additives. High catalytic yields (styrene oxide, 120 °C, 8 h, 94% yield; 100 °C, 20 h, 93% yield) can be achieved by appropriately extending the reaction times at low temperature, and the reaction times are shorter than other porous materials under the same conditions. This work provides a new strategy for synthesizing an efficient metal-free heterogeneous catalyst with high ionic content and a large specific surface area from HCPs for the conversion of CO2 into cyclic carbonates. It also demonstrates that the ionic content and specific surface area must be coordinated to obtain high catalytic activity for CO2 cycloaddition reaction. Full article
(This article belongs to the Topic Catalysis for Sustainable Chemistry and Energy)
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12 pages, 3210 KB  
Article
Facile Cellulose Dissolution and Characterization in the Newly Synthesized 1,3-Diallyl-2-ethylimidazolium Acetate Ionic Liquid
by Hui Zhang, Yaoguang Xu, Yuqi Li, Zexiang Lu, Shilin Cao, Mizi Fan, Liulian Huang and Lihui Chen
Polymers 2017, 9(10), 526; https://doi.org/10.3390/polym9100526 - 18 Oct 2017
Cited by 39 | Viewed by 8798
Abstract
A facile cellulose solvent 1,3-diallyl-2-ethylimidazolium acetate ([AAeim][OAc]) with high electrical conductivity has been designed and synthesized for the first time, via a quaternization reaction and ion exchange method. The dissolution characteristics of cellulose in this solvent were studied in detail. Meanwhile, the co-solvent [...] Read more.
A facile cellulose solvent 1,3-diallyl-2-ethylimidazolium acetate ([AAeim][OAc]) with high electrical conductivity has been designed and synthesized for the first time, via a quaternization reaction and ion exchange method. The dissolution characteristics of cellulose in this solvent were studied in detail. Meanwhile, the co-solvent system was designed by adding an aprotic polar solvent dimethyl sulfoxide (DMSO) in [AAeim][OAc]. The effects of temperature and the mass ratio of DMSO to [AAeim][OAc] on the solubility of cellulose were studied. Furthermore, the effects of regeneration on the molecular structure and thermal stability of cellulose were determined by Fourier transform infrared spectroscopy (FT-IR), thermal gravity analysis (TGA) and X-ray diffraction (XRD). The findings revealed that the synthesized ionic liquid (IL) has a relatively low viscosity, high conductivity and a good dissolving capacity for bamboo dissolving pulp cellulose (Degree of Polymerization: DP = 650). The macromolecular chain of the cellulose is less damaged during the dissolution and regeneration process. Due to the increased number of “free” anions [OAc]and cations [AAeim]+, the addition of DMSO can significantly increase the solubility of the cellulose up to 12 wt % at the mass ratio of 3:1, indicating that the synthesized IL has a potential application in the electrospinning field. Full article
(This article belongs to the Collection Polysaccharides)
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11 pages, 410 KB  
Article
An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
by Dajana Gašo-Sokač, Valentina Bušić, Mario Cetina and Marijana Jukić
Molecules 2014, 19(6), 7610-7620; https://doi.org/10.3390/molecules19067610 - 6 Jun 2014
Cited by 9 | Viewed by 7196
Abstract
Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%–94%) were obtained in acetone [...] Read more.
Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%–94%) were obtained in acetone in very short reaction times (3–5 min) as well as in the solvent-free procedure (42%–78%) in very short reaction times (7–10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method. Full article
(This article belongs to the Section Organic Chemistry)
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12 pages, 81 KB  
Article
Reactivity of 3-Ethoxycarbonyl Isoquinolinium Salts Towards Various Nucleophilic Reagents: Applications to the Synthesis of New 1,2-Dihydroisoquinoline-3-carboxylates
by Mohamed Ameziane Aït Amer Meziane and Jean Pierre Bazureau
Molecules 2002, 7(2), 252-263; https://doi.org/10.3390/70200252 - 28 Feb 2002
Cited by 7 | Viewed by 10165
Abstract
Different types of novel 1,2-disubstituted 1,2-dihydro isoquinolines were synthesized by addition reactions of organolithium, alcoholates and borohydride reagents with various isoquinolinium salts. The leaving group character of the isoquinoline moiety was also evidenced. Full article
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