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ACS Sustainable Chemistry & Engineering · 2023 · IF 8.4

Selective and Efficient Gold Extraction from E-Waste by Pyrrolidinium-Based Ionic Liquids with Various N-Substituents

Xiaoxia Liu,Yangyang Wang,Ronghao Liu,Ping Lv,Wenfeng Xue,Jinxin Guo,Huiying Wei,Yanzhao Yang

With environmental problems and a shortage of resources, it is urgent to recover gold from electronic waste (e-waste). Meanwhile, it is necessary to explore the relationships between the structures and extraction performances of ionic liquids (ILs) to further improve the extraction capacities of ILs for gold. Herein, three pyrrolidinium-based ILs with various N-substituents were synthesized for solvent-free extraction of Au(III). The three pyrrolidinium-based ILs exhibited ultrahigh extraction capacities for Au(III) with the order of [Pyr-EA][NTf2] (524.6 mg·g–1) > [Pyr-Bu][NTf2] (457.3 mg·g–1) > [Pyr-C2OC2][NTf2] (403.5 mg·g–1). The effects of N-substituents on extraction performances were quantitatively investigated by electrostatic potential (ESP) and quantitative NMR. Among them, the ester group (−COOR) is the most beneficial to the extraction process, which is associated with an increased ESP value and boosted hydrophobicity. Notably, [Pyr-EA][NTf2] displayed outstanding selectivity in multimetal solutions; especially, it could selectively and efficiently extract Au(III) from the actual CPU. Furthermore, [Pyr-EA][NTf2] possesses significant reuseability and can maintain superior extraction efficiency of 84.3% after five cycles. These excellent performances together with low cost ($0.44·g–1 [Pyr-EA][NTf2]) and considerable profit ($29.72·g–1 [Pyr-EA][NTf2]) confirmed that [Pyr-EA][NTf2] is a promising prospect for sustainable recovery of gold from e-waste.

研究领域: 环境科学 · 材料化学
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DESALINATION · 2023 · IF 9.9

Incorporating functionalized acyl chloride monomer with rigid pyrrolidinyl group via two-step interfacial polymerization for improving permeability of reverse osmosis membranes

Xiaojuan Wang,Kuisuo Yang,Huacheng Xu,Yijun Huang,Congjie Gao,Xueli Gao

Novel acyl chloride monomer 5-(1-pyrrolidinyl)-1,3-benzenedicarbonyl dichloride (PIPC) featuring a rigid pyrrolidinyl group was proposed as an organic phase monomer to fabricate reverse osmosis (RO) membranes possessing exceptional water permeability and NaCl rejection via a two-step interfacial polymerization method. First, m -phenylenediamine (MPD) in the aqueous phase solution polymerized with PIPC in the first organic phase solution to form the much looser polyamide . After that the remaining MPD continued to diffuse to polymerize with trimesoyl chloride in the second organic phase solution to form the denser polyamide. The pyrrolidinyl group had steric hindrance effects and formed hydrogen bond with MPD, leading to decreasing the thickness significantly and increasing surface roughness of the separating layer. When the PIPC amount was 0.08 wt%, the PIPC-based RO membrane displayed optimal permselectivity with water flux increasing by 84.20 % compared to the original RO membrane (from 20.38 L·m −2 ·h −1 to 37.54 L·m −2 ·h −1 ) whereas retaining high NaCl rejection with 98.59 %. The PIPC-based RO membrane exhibited steady water flux and NaCl rejection within 120 h of filtration, as well as improved antifouling performance. Thus, preparation of the highly permeable RO membrane could be rationally achieved by the novel acyl chloride monomer with a rigid pyrrolidinyl group.

研究领域: 材料科学 · 环境工程
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Food Frontiers · 2025 ·Vol. 6 ·期 2 ·1058-1078 · IF 6.9

Amination of Flavonoids Possessing a Pyrogallol Group in Cell Culture Medium at 37°C

Haolin Zhang,Jingjing Zhang,Hui Cao,Petra Högger,Randolph Arroo,Mohamed A. Farag,Avi Shpigelman,Jianbo Xiao,Chunlin Li

A class of flavonoid aminated derivatives that had been consistently overlooked in literature was shown to be formed as artefacts in cell culture medium. In this study, 34 flavonoids from different subclasses were incubated in Dulbecco's modified Eagle's Medium (DMEM) at 37°C for 2 h to identify the reaction mechanism behind aminated derivatives formation from flavonoids. Baicalein, scutellarein, dihydromyricetin, (−)-gallocatechin (GC), (−)-epigallocatechin (EGC), (−)-GC gallate, and (−)-EGC gallate were found to yield corresponding nitrogenous derivatives in both DMEM and amino acid solution. The nitrogen source of these seven flavonoid -aminated derivatives was revealed to be amino acids in DMEM. The pyrogallol group of the flavonoids was a key structural motif, being first oxidized into quinone and then further reacting with amino acids (Strecker degradation) to yield aminated flavonoids and corresponding aldehydes. A slightly alkaline environment accelerated the amination of flavonoids, possibly via the formation of flavonoid quinone. These results provide the mechanistic evidence for the in vitro generation of flavonoid -aminated derivatives, yet to be tested using in vivo assays.

研究领域: 生物化学 · 药理学
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NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 18 ·7028-7034 · IF 3.069

Alkyl substituted 4-pyrrolidinopyridinium salts encapsulated in the cavity of cucurbit[10]uril

Weitao Xu,Ming Liu,Mary Clare Escaño,Carl Redshaw,Bing Bian,Ying Fan,Zhu Tao,Xin Xiao

The interaction between cucuribit[10]uril (Q[10]) and a series of 4-pyrrolidinopyridinium salts bearing aliphatic substituents at the pyridinium nitrogen, namely 4-(C4H8N)C5H5NRBr, where R = Et (g1), n-butyl (g2), n-pentyl (g3), n-hexyl (g4), n-octyl (g5), n-dodecyl (g6), has been studied in aqueous solution by 1H NMR spectroscopy, electronic absorption spectroscopy and mass spectrometry. The results revealed that the guests g1–g5 are located completely inside the cavity differing only in the orientation of g1, g4 and g5 which are aligned with the portal, whilst g2 and g3 are perpendicular to it. For g6, the tetrahydropyrrole moiety remains outside of the portal. DFT calculations confirm the stability of the guests in the Q[10] and the possibility of their curved structure inside the Q[10].

CAS / MDL: 2456-81-7
研究领域: 化学 · 分子生物学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Ultrafast solid-phase synthesis of 2D pyrene-alkadiyne frameworks towards efficient capture of radioactive iodine

Yichen Yin,Yang Yang,Guojuan Liu,Huiling Chen,Dian Gong,Yiming Ying,Jingrui Fan,Sijia Liu,Zhi Li,Chuhao Wang,Zhuangyan Guo,Zhikao Li,Chengbing Yu,Gaofeng Zeng

Iodine (I 2 ) capture over adsorbents has great potential for the treatment of radioactive nuclear wastes. Herein, we develop a direct synthesis of 2D structured pyrene-alkadiyne frameworks, poly(1,3,6,8-tetraethynylpyrene) (PTEP), through a facile and ultrarapid solid-phase thermal polymerization of 1,3,6,8-tetraethynylpyrene (TEP) monomers in air. With this way, only single chemical of TEP is used without any catalysts, templates, solvents, and waste emissions. The PTEP frameworks feature high content of periodically distributed pyrene groups, regular intra-plane big rings, and 2D interlamellar structure, which endow PTEP with abundant electron-donors, high and accessible specific surface area as well as low resistance of mass transfer. PTEP exhibits high I 2 capture capacity (3380 mg g −1 for vaporous I 2 at 75 °C and 2570 mg g −1 for aqueous solution at 25 °C), fast adsorption kinetics (1350 mg g -1 h −1 at 75 °C), strong water tolerance, thermal stability, and reliable reusability for the adsorption of vaporous I 2 and I 2 aqueous solution, which are superior to most of current sorbents. The experiments and modellings suggest that I 2 adsorption on PTEP refers to the Langmuir adsorption model and the pseudo-second-order adsorption kinetics, in which the adsorbed iodine exists as polyiodide I 5 - via accepting electrons mainly from pyrenes.

研究领域: 材料科学 · 环境科学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2012 · IF 3.07

Aggregation behavior of gemini pyrrolidine-based ionic liquids 1,1′-(butane-1,4-diyl)bis(1-alkylpyrrolidinium) bromide ([Cnpy-4-Cnpy][Br2]) in aqueous solution

Shaohua Zhang,Han Yan,Mingwei Zhao,Liqiang Zheng

Three gemini pyrrolidine-based ionic liquids, 1,1′-(butane-1,4-diyl)bis(1-alkylpyrrolidinium) bromide ([C n py-4-C n py][Br 2 ], n   =   10, 12, 14), were synthesized. Their aggregation behavior in aqueous solution was systematically investigated by surface tension, electrical conductivity, and steady-state fluorescence. Compared with their corresponding monomers, N -alkyl- N -methylpyrrolidinium bromide (C n MPB), [C n py-4-C n py][Br 2 ], have higher surface activity. The special structure of [C n py-4-C n py][Br 2 ] that has a spacer in their hydrophilic head groups results in a lower surface excess concentration ( Γ max ) and a larger molecular cross-sectional area ( A min ). Electrical conductivity studies show a lower degree of counter-ion binding to the aggregates. A smaller aggregation number ( N agg ) is observed by the pyrene fluorescence quenching method. A series of thermodynamic parameters ( Δ G agg 0 , Δ H agg 0 , - T Δ S agg 0 ) of aggregation derived from electrical conductivity indicate that the aggregation of [C n py-4-C n py][Br 2 ] is enthalpy-driven, while aggregation of C n MPB is entropy-driven at low temperatures but enthalpy-driven at high temperatures.

研究领域: 化学 · 物理化学 · 界面科学
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MACROMOLECULAR RAPID COMMUNICATIONS · 2022 ·Vol. 44 ·期 3 ·2200669 · IF 5.006

Pyrrolidinium-Based Hyperbranched Anion Exchange Membranes with Controllable Microphase Separated Morphology for Alkaline Fuel Cells

Xiaoqin Duan,Xiang Zhu,Gege Li,Ru Xia,Jiasheng Qian,Qianqian Ge

It is well acknowledged that the microphase-separated morphology of anion exchange membranes (AEMs) is of vital importance for membrane properties utilized in alkaline fuel cells. Herein, a rigid macromolecule poly(methyldiallylamine) (PMDA) is incorporated to regulate the microphase morphology of hyperbranched AEMs. As expected, the hyperbranched poly(vinylbenzyl chloride) (HB-PVBC) is guided to distribute along PMDA chains, and longer PMDA cha leads to a more distinct microphase morphology with interconnected ionic channels. Consequently, high chloride conductivity of 10.49 mS cm −1 at 30 °C and suppressed water swelling ratio lower than 30% at 80 °C are obtained. Furthermore, the β -H of pyrrolidinium cations in the non-antiperiplanar position increases the energy barrier of β -H elimination, leading to conformationally disfavored Hofmann elimination and increased alkaline stability. This strategy is anticipated to provide a feasible way for preparing hyperbranched AEMs with clear microphase morphology and good overall properties for alkaline fuel cells.

CAS / MDL: 78-67-1 76-05-1
研究领域: 材料科学 · 能源科学
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ACS Applied Materials & Interfaces · 2015 · IF 6.723

Stable, High-Efficiency Pyrrolidinium-Based Electrolyte for Solid-State Dye-Sensitized Solar Cells

Tong He,Ye Feng Wang,Jing Hui Zeng

We synthesized a series of pyrrolidinium based dicationic ionic crystals with high melting point and good thermal stability. Research on the crystal structure shows that there are ordered three-dimensional ionic channels in these crystals which is favorable for the ionic conductor to achieve high conductivity and diffusion coefficient. These ionic crystals are applied to electrolyte as matrix in dye sensitized solar cells, and the influence of crystal structure (including the alkylene chain separating two pyrrolidinium rings and anion) versus the device performances are studied by steady-state voltammography, current–voltage trace, and electrochemical impedance spectroscopy. As the solid state electrolyte, an optimized efficiency of 6.02% have achieved under full sunlight irradiation using ionic crystal [C6BEP][TFSI]2. And the device based on this solid electrolyte shows the excellent long-term stability, maintaining 92% of the initial efficiency after 960 h. This study elucidates fundamental the structure of dicationic crystal and provide useful clues for further improvement of solid-state electrolytes in DSSC.

研究领域: 材料科学 · 能源科学
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Chemistry-An Asian Journal · 2018 ·Vol. 14 ·期 1 ·235-242 · IF 3.692

A Study of the Interaction Between Cucurbit[8]uril and Alkyl-Substituted 4-Pyrrolidinopyridinium Salts

Weitao Xu,Jinglan Kan,Bo Yang,Timothy J. Prior,Bing Bian,Xin Xiao,Zhu Tao,Carl Redshaw

Graphical Can I have some pumpkin soup, please? In the host–guest complexes formed between cucurbit[8]uril and the alkyl-substituted 4-pyrrolidinopyridinium salts 4-(C 4 H 8 N)C 5 H 5 NRBr (R=Et, n -butyl, n -pentyl, n -dodecyl), the orientation of the guest molecule changes with the length of R. Solid state structures are different to those observed in solution, and for R= n -pentyl, there are two different interactions between Q[8] and the guest. The interaction between cucuribit[8]uril (Q[8]) and a series of 4-pyrrolidinopyridinium salts bearing aliphatic substituents at the pyridinium nitrogen, namely 4-(C 4 H 8 N)C 5 H 5 NRBr, where R=Et (g1), n -butyl (g2), n -pentyl (g3), n -hexyl (g4), n -octyl (g5), n -dodecyl (g6), has been studied in aqueous solution by 1 H NMR spectroscopy, electronic absorption spectroscopy, isothermal titration calorimetry and mass spectrometry. Single crystal X-ray diffraction revealed the structure of the host–guest complexes for g1, g2, g3, and g5. In each case, the Q[8] contains two guest molecules in a centrosymmetric dimer. The orientation of the guest molecule changes as the alkyl chain increases in length. Interestingly, in the solid state, the inclusion complexes identified are different from those observed in solution, and furthermore, in the case of g3, Q[8] exhibits two different interactions with the guest. In solution, the length of the alkyl chain plays a significant role in determining the type of host–guest interaction present.

CAS / MDL: 2456-81-7
研究领域: 化学 · 超分子化学
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Small · 2024 · IF 13

Synchronous Regulation Strategy of Pyrrolidinium Thiocyanate Enables Efficient Perovskite Solar Cells and Self-Powered Photodetectors

Cong Chen,Zuolin Zhang,Chen Wang,Taoran Geng,Yinsu Feng,Jike Ding,Quanxing Ma,Wenhuan Gao,Mengjia Li,Jiangzhao Chen,Jian-xin Tang

Developing inventive approaches to control crystallization and suppress trap defects in perovskite films is crucial for achieving efficient perovskite photovoltaics. Here, a synchronous regulation strategy is developed that involves the infusion of a zwitterionic ionic liquid additive, pyrrolidinium thiocyanate (PySCN), into the perovskite precursor to optimize the subsequent crystallization and defects. PySCN modification not only orchestrates the crystallization process but also deftly addresses trap defects in perovskite films. Within this, SCN − compensates for positively charged defects, while Py + plays the role of passivating negatively charged defects. Based on the vacuum flash evaporation without anti-solvent, the air-processed perovskite solar cells (PSCs) with PySCN modification can achieve an extraordinary champion efficiency of 22.46% (0.1 cm 2 ) and 21.15% (1.0 cm 2 ) with exceptional stability surpassing 1200 h. Further, the self-powered photodetector goes above and beyond, showcasing an ultra-low dark current of 2.13 × 10 −10 A·cm −2 , a specific detection rate of 6.12 × 10 13 Jones, and an expansive linear dynamic range reaching an astonishing 122.49 dB. PySCN modification not only signifies high efficiency but also ushers in a new era for crystallization regulation, promising a transformative impact on the optoelectronic performance of perovskite-based devices.

CAS / MDL: 13478-00-7
研究领域: 材料科学 · 光伏技术 · 光电子学
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SYNTHETIC COMMUNICATIONS · 2019 · IF 1.439

One-pot multicomponent construction of chromanone-fused pyrrolidinyl spirooxindole collections through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction

Shuang Chen,Jing Yue,Xiong-Li Liu,Jun-Xin Wang,Xiong Zuo,Yu Cao

A new method was developed for the facile one-pot multicomponent construction of heterocycle-fused spiro compounds containing chromanone and pyrrolidinyl spirooxindoles, two potential pharmacophores, in one molecule through a decarboxylative 1,3-dipolar [3 + 2] cycloaddition reaction of carboxylic acid group-activated chromones 1 with isatin-derivated azomethine ylides based on molecular hybridization strategy. A wide variety of products with three contiguous stereocenters including a spiro quaternary stereocenter were smoothly prepared with high efficiency (up to 87% yield and 20:1 diastereomeric ratio). This method could offer libraries of architecturally diverse and multiple pharmacore collections, potentially useful in medicinal chemistry.

CAS / MDL: 14913-33-8
研究领域: 有机化学 · 药物化学 · 合成化学
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MOLECULES · 2017 ·Vol. 22 ·期 4 ·645 · IF 2.861

Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction

Bing Lin,Gen Zhou,Yi Gong,Qi-Di Wei,Min-Yi Tian,Xiong-Li Liu,Ting-Ting Feng,Ying Zhou,Wei-Cheng Yuan

Described herein is the development of a facile and efficient methodology for the synthesis of novel turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles3–5via a multicomponent 1,3-dipolar cycloaddition of dienones2with azomethine ylides (thermally generated in situfrom isatins and proline or thioproline or sarcosine). Products bearing four or three consecutive stereocenters consist of two oxindole moieties and a pyrrolidinyl core, including vicinal spiroquaternary stereocenters fused in one ring structure were smoothly obtained in high yields (up to 93% yield) with good diastereoselectivity (up to >20:1). Another valuable application of this method was for the design of new hybrid architectures for biological screening through the adequate fusion of these sub-units of turmerone and 3,3′-pyrrolidinyl-dispirooxindole, generating drug-like molecules.Keywords:turmerone motif-fused 3,3′-pyrrolidinyl-dispirooxindoles;vicinal spiroquaternary stereocenters;1,3-dipolar cycloaddition reaction;azomethine ylides;diastereoselectivity

CAS / MDL: 14913-33-8
研究领域: 有机化学 · 药物化学 · 生物化学
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