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CORROSION SCIENCE · 2016 · IF 5.154

In situ click-assembling monolayers on copper surface with enhanced corrosion resistance

Yinzhe Yu,Yizhen Wang,Jin Li,Daquan Zhang,Lixin Gao

The self-assembled monolayer (SAMs) of 2-(1-tosyl-1H-1,2,3-triazol-4- yl ) propan-2-ol (TTP) was in-situ assembled on copper surface via click chemistry reaction between 2, 2-dimethylethynyl carbinol (MBY) and tosyl azide (TA). The electrochemical results indicate that the click-assembled TTP film can strongly suppress the corrosion reaction of copper in 3   wt.% NaCl and its protection efficiency is 93.6%. Polarization curves show that TTP SAMs is an anodic passivation type inhibitor. The adsorption of TTP molecules on Cu 2 O (0 0 1) surface is in the flat orientation of the nearby triazole ring and O atoms.

研究领域: 材料科学 · 电化学
✓ 已验证 DOI 高影响因子
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BIOORGANIC CHEMISTRY · 2024 · IF 4.5

Synthesis of triazole AD-1 derivatives and its mechanism of mediating DNA damage of ROS in lung cancer cells

Linlin Han,Hongyan Tan,Jungjoon Lee,Peng Wang,Yuqing Zhao

Based on the significant biological activities and the remarkable physical and chemical properties of 1 H -1,2,3-triazole pharmacophore, we herein adopted the strategy of click chemistry to combine the triazole fragment and the unique scaffold of 25-OCH 3 -PPD ( AD-1 ) to design a series of potent compounds inducing apoptosis and DNA damage. The anti-proliferative effect was verified by MTT assay and colony formation assay. DNA double-stand breaks (DSBs) were obtained by observing the nuclear focus formation and the protein expression of γ-H2AX. Cell cycle arrest was evaluated by the cycle-related proteins such as CDK2, CDK4, CDK6, Cyclin D1 and P 21. Apoptosis was assessed by flow cytometry, mitochondrial membrane potential (MMP) detection and the expression of apoptosis-related proteins. Reactive oxygen species (ROS) generation was measured with 2′, 7′-dichlorofluorescein diacetate (DCFH-DA) staining. According to SAR analysis, the most potent compound 6a exhibited great inhibitory effect against A549 cells, which IC 50 value of 2.84 ± 0.68 μM. Furthermore, 6a remarkably induced DNA damage, cell cycle arrest and apoptosis in A549 cells. 6a treatment increased the levels of ROS. Network pharmacology and molecular docking predicted the potential signaling pathways and ligand-receptor interactions, and the results of western blotting showed that 6a inhibited the PI3K/Akt/Bcl-2 signaling pathway by decreasing PI3K and Bcl-2 and total level of Akt expression, while Bax and Cyt c were increasing in 6a -treated A549 cells. As mentioned above, 6a has a potent inhibitory effect in A549 cells through induction of DNA damage, apoptosis via ROS generation and modulation of PI3K/Akt/Bcl-2 signaling pathway.

研究领域: 药理学 · 肿瘤学 · 化学生物学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF ORGANIC CHEMISTRY · 2022 · IF 4.198

Copper-Promoted One-Pot Sandmeyer-Type Reaction for the Synthesis of N-Aryltriazoles

Menghan Cui,Rong Wang,Qing Yang,Chunxiang Kuang

Herein, we report the copper-catalyzed one-pot Sandmeyer-type reaction of aromatic amines with triazoles to afford N-aryl-1,2,3-triazoles. Diazonium salts, formed from aromatic amines and tert-butyl nitrite in the presence of fluoroboric acid, reacted with triazoles in a copper-catalyzed Sandmeyer-type reaction. The reaction proceeded under mild conditions to afford N-aryltriazoles in moderate to good yields. This method is amenable to a wide range of aromatic amines and triazoles and shows diverse functional group tolerance. Inhibition of the reaction upon the addition of free radical scavengers suggested a radical pathway, in which the aryl radical, copper, and triazole formed a complex that underwent reductive elimination to give aryltriazole compounds; this is consistent with the mechanism underlying the Sandmeyer reaction. Thus, we demonstrate a new effective strategy for the construction of C–N bonds via Sandmeyer-type reactions and a valuable alternative approach for the synthesis of aryltriazole derivatives.

研究领域: 有机化学 · 合成化学
✓ 已验证 DOI PubMed 高影响因子
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SEPARATION AND PURIFICATION TECHNOLOGY · 2022 · IF 9.136

Ultra-high NH3 absorption by triazole cation-functionalized ionic liquids through multiple hydrogen bonding

Xueqi Sun,Guilin Li,Shaojuan Zeng,Lei Yuan,Lu Bai,Xiangping Zhang

Ionic liquids (ILs) are considered as prospective absorbents for NH 3 separation and purification owing to extremely low vapor pressure, great affinity and structural tunability. Up to date, versatile ILs for NH 3 absorption have been developed, but NH 3 mass capacity of all the reported ILs or IL-based absorbents are still not comparable to that of traditional water absorbent. How to simultaneously improve NH 3 mass capacity, selectivity and keep stable reversibility using IL absorbents is still a great challenge. In this work, the triazole cation-functionalized ionic liquids (TCFILs) by introducing multiple protic H sites into N -heterocyclic cations were firstly designed and synthesized for enhancing NH 3 absorption. These TCFILs showed superhigh NH 3 mass capacity up to 0.365 g NH 3 /g IL at 30 °C and 1 bar, which is the maximum among the reported absorbents, and is even comparable to that of traditional water absorbent used in industrial. Moreover, the TCFILs also exhibited excellent selectivity of NH 3 /CO 2 up to 182 and recycling stability. Such great comprehensive performances of NH 3 absorption and separation were proved to originate from multiple hydrogen bonding between NH 3 and protic hydrogens of the TCFIL cations. Therefore, this work will provide useful guidance to design competitive functionalized ILs for efficient and reversible absorption of NH 3 .

研究领域: 化学工程 · 材料科学
✓ 已验证 产品关联 DOI 高影响因子
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APPLIED ORGANOMETALLIC CHEMISTRY · 2017 ·Vol. 32 ·期 1 ·e3946 · IF 2.319

Supported copper (I) catalyst from fish bone waste: An efficient, green and reusable catalyst for the click reaction toward N-substituted 1,2,3-TRIAZOLES

Xingquan Xiong,Zhongke Tang,Zhaohong Sun,Xiaoqing Meng,Sida Song,Zhilong Quan

An eco-efficient, green, and multi-gram procedure is presented for one-pot multicomponent synthesis of N -substituted 1,2,3-triazoles by using waste fishbone powders supported CuBr (FBPs-CuBr) as catalyst. FBPs-CuBr is found to be an efficient heterogeneous catalyst and a series of 1,2,3-triazoles are obtained in moderate to excellent yields in water under MW irradiation (70–98%). It can be separated conveniently by a simple filtration and reused at least seven consecutive runs with a slight drop in the product yields. Furthermore, the desired product still could be obtained in 80% yield when the scale of the reaction was increased to 40.0 mmol.

研究领域: 有机化学 · 绿色化学 · 催化材料
✓ 已验证 DOI 高影响因子
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RUSSIAN JOURNAL OF GENERAL CHEMISTRY · 2018 ·Vol. 87 ·期 12 ·3036-3042 · IF 0.658

Synthesis of Homoleptic and Heteroleptic Ruthenium Complexes Appended with Glucosyl Ligand by the Click-to-Chelate Approach

Xiao N.,Cheng A.,Zhu Q. G.,Cheng Q.,Wu R. B.,Yu B. R.,Wang Z.

Homoleptic and heteroleptic complexes of Ru(TAGP-tapy) 3 Cl 2 {TAGP-tapy is 2-[1-(2,3,4,6-tetra- O -acetyl-β-D-glucopyranosyl)-1 H -1,2,3-triazol-4-yl]-pyridine} bearing a clustered glucose-derived ligand and Ru(bpy) 2 (TAGP-tapy)Cl 2 (bpy is 2,2'-bipyridine) have been synthesized by the chelating reaction of RuCl 3 ·3H 2 O with TAGP-tapy and cis -Ru(bpy) 2 Cl 2 with TAGP-tapy, respectively. The bidentate 1,2,3-triazolelinked glucose-derived ligand TAGP-tapy was prepared by copper-catalyzed coupling (click reaction) of 2-ethynylpyridine with acetyl protected glucosyl azide, 2,3,4,6-tetra- O -acetyl-β-D-glucopyranosyl azide (TAGP-N 3 ). TAGP-N 3 was prepared by nucleophilic substitution reaction of 2,3,4,6-tetra- O -acetyl-α-D-glucopyranosyl bromide (TAGP-Br) with NaN 3 . These ruthenium complexes were purified by column chromatography or HPLC. Structures of the intermediates and ruthenium complexes were confirmed by HPLC, 1 H and 13 C NMR, FT-IR, and ESI-MS spectroscopies. UV-Vis and fluorescence spectroscopic methods were used to study optical properties of the ligand TAGP-tapy and ruthenium complexes. TAGP-tapy exhibited interesting solvent-polarity dependent fluorescence properties and a significant red-shift in emissions. Both complexes demonstrated distinctive fluorescence emission band in the visible region.

研究领域: 有机化学 · 配位化学 · 材料科学
✓ 已验证 DOI 高影响因子
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Polymer Chemistry · 2019 ·Vol. 10 ·期 26 ·3585-3596 · IF 4.76

Photo-controlled release of metal ions using triazoline-containing amphiphilic copolymers

Xiaoying Xu,Qian Zhang,Kang Liu,Nailiang Liu,Ying Han,Weixing Chen,Chao Xie,Pengfei Li,Jie He

Photo-controlled release that shows a quick response and high spatial/temporal accuracy has become attractive given its potential applications for biomedicines. A few metal complexes are known for their uses in detoxification, sterilization, and diagnosis and treatment of diseases, but, the encapsulation and controlled release of those metal ions using polymer micelles are challenging. We report an interesting photo-controlled release of metal ions via photo-responsive triazoline-containing amphiphilic polymers. Amphiphilic random copolymers of glycidyl methacrylate and oligo(ethylene oxide) methyl ether methacrylate were prepared through free radical copolymerization. The glycidyl pendants were converted to azide, followed by a 1,3-dipolar cycloaddition reaction to form triazoline with norbornene. The resulting random copolymers containing triazoline formed micelles with a critical micellar concentration (CMC) of 7.68 × 10−3 mg mL−1. The triazoline moieties could coordinate to transition metal ions, e.g. Co2+, and thus encapsulate the metal ions to the core of micelles. Photo-induced denitrogenation of triazoline was able to disrupt the coordination of Co2+ and triazoline, therefore leading to the release of Co2+. Solution viscosity, UV-vis/NMR spectroscopy and TEM were used to show that the coordination and release of Co2+ ions were successful upon exposure to light. The photo-controlled release profile was found to be linearly dependent on the irradiation time, which is potentially useful for the delivery of essential ions in vivo.

CAS / MDL: 100-66-3
研究领域: 材料科学 · 生物医学工程
✓ 已验证 产品关联 DOI 高影响因子
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PROGRESS IN ORGANIC COATINGS · 2019 · IF 3.42

Enhanced corrosion resistance of copper by synergetic effects of silica and BTA codoped in polypyrrole film

Shan Wan,Chun-Hui Miao,Ruo-Min Wang,Ze-Fan Zhang,Ze-Hua Dong

Conductive polypyrrole (PPy) composite films were electrodeposited on copper together with BTA or/and silica by cyclic voltammetry in salicylate solution. The corrosion resistance and electrical conductivity of the composite films were assessed by use of polarisation curves, open circuit potential (OCP) measurements and electrochemical impedance spectroscopy in 5 wt% NaCl solution. It was found that the sole doping of benzotriazole (BTA) or silica in PPy film merely improved corrosion resistance slightly, but the codoping of BTA and silica in PPy film can significantly enhance the corrosion resistance and electrical conductivity of the composite film. Salt spraying test (SST) confirmed that the ternary composite film exhibited the best anti-corrosion performance and durability, which was attributed to the synergetic effect from the physical barrier of silica and the active protection of BTA inhibitor.

CAS / MDL: 95-14-7 109-97-7 54-21-7
研究领域: 材料科学 · 电化学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2013 · IF 2.206

Potential for Using Simple 1,2,4-Triazole Salt Solutions as Highly Efficient CO2 Absorbents with Low Reaction Enthalpies

Jie Ren,Linbo Wu,Bo-Geng Li

Simple solutions of alkali metal salts of 1,2,4-triazole (TrizM) in polyethyelene glycol (PEG) and dimethylsulfoxide (DMSO) were prepared and assessed for CO2 capture. These aprotic heterocyclic anions (AHAs) containing solutions exhibit excellent CO2 capture performances. The TrizM salts absorb CO2 chemically in a 1:1 stoichiometry. What is more attractive is that the CO2 chemical absorption enthalpies are as low as −33 ∼ −21 kJ mol–1, close to that of physical absorption by traditional ionic liquids (ILs). This makes regeneration of the absorbents highly energy-saving. The TrizM-PEG solution has a steady CO2 capture performance due to the nonvolatility of PEG, and therefore, it is durable for CO2 capture. In comparison, the TrizM-DMSO solution has a higher absorption capacity (120 mg/g solution) because of the higher solubility of TrizM. Such simple and inexpensive solutions show new potential as promising candidates for highly efficient, energy-saving, and economical CO2 catchers.

CAS / MDL: 288-88-0
研究领域: 化学工程 · 环境科学
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CHEMISTRY-A EUROPEAN JOURNAL · 2016 ·Vol. 23 ·期 15 ·3631-3636 · IF 5.771

Structure-Activated Copper Photosensitisers for Photocatalytic Water Reduction

Nan-Yu Chen,Liang-Min Xia,Alastair J. J. Lennox,Yuan-Yuan Sun,Hao Chen,Hai-Ming Jin,Henrik Junge,Qin-An Wu,Jian-Hong Jia,Matthias Beller,Shu-Ping Luo

Graphical Hydrogen production : A series of phenanthroline-based ligands have been synthesised and the photosensitising ability of their heteroleptic [Cu(P^P)(N^N)] + complexes in light-driven Cu–Fe-based water reduction has been studied (see scheme). In this noble-metal-free system, the steric and electronic effects of the substituents at the 2,9- and 4,7-positions of phenanthroline have been explored. It is shown for the first time that the presence of fluorine in nitrogen ligands increases the efficacy of copper complexes in photocatalytic hydrogen production. A series of phenanthroline-based ligands have been synthesised and their influence as bidentate nitrogen ligands in heteroleptic [Cu(P^P)(N^N)] + photosensitisers in light-driven water reduction has been studied. In this noble-metal-free Cu–Fe-based photocatalytic water reduction system, the structural effects of the nitrogen ligands have been explored, including the steric and electronic effects of substituents at the 2,9- and 4,7-positions of phenanthroline. Ligands were prepared that led to increased hydrogen generation, with turnover numbers (TON Cu ) of up to 1388 being observed. All the new complexes were electrochemically and photophysically characterised. We demonstrate for the first time that the presence of fluorine in nitrogen ligands increases the efficacy of copper complexes in photocatalytic hydrogen production.

CAS / MDL: 7664-93-9 804-63-7
研究领域: 化学 · 材料科学 · 能源科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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RSC Advances · 2017 ·Vol. 7 ·期 16 ·9567-9572 · IF 3.108

Cupric oxide nanowires on three-dimensional copper foam for application in click reaction

Chunxia Wang,Fan Yang,Yan Cao,Xing He,Yushu Tang,Yongfeng Li

Readily prepared CuO nanowires (CuO NWs) have been found to be effective heterogeneous catalysts for the 1,3-dipolar cycloaddition (CuAAC) reaction without using any additional support and bases. Examination of CuO nanowire catalysts synthesized at various temperatures showed that the use of CuO-600 catalyst was the best choice for the success of the present click reaction. Not only aromatic and heteroaromatic alkynes but also alkylalkynes were catalyzed regioselectively, affording triazoles in excellent yields. Furthermore, we have identified that the reaction proceeded in a heterogeneous manner. It is noteworthy that the CuO-600 catalyst can be easily recovered and reused nine times.

CAS / MDL: 622-79-7
研究领域: 材料科学 · 有机化学
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JOURNAL OF MATERIALS SCIENCE & TECHNOLOGY · 2021 · IF 8.067

Photothermal and pH dual-responsive self-healing coating for smart corrosion protection

Yao Huang,Panjun Wang,Weimin Tan,Wenkui Hao,Lingwei Ma,Jinke Wang,Tong Liu,Fan Zhang,Chenhao Ren,Wei Liu,Dawei Zhang

A novel self-healing coating with photothermal and pH dual-responsive properties has been designed to protect carbon steel against corrosion by loading the stimuli-responsive microcapsules into a shape memory epoxy coating. The sandwich-like microcapsules were based on reduced graphene oxide/mesoporous silica (rGO@MS) assembled with a pH-responsive poly(N,N-dimethylaminoethyl methacrylate) (PDMAEMA) layer, and were loaded with benzotriazole (BTA) inhibitors (abbreviated as rGO@MS-P-BTA). Under near-infrared (NIR) light irradiation, the prominent photothermal effect of rGO could not only elevate the coating temperature to activate the shape memory effect and close the coating scratch, but also facilitate the release of corrosion inhibitors to suppress the corrosion activity. Moreover, the PDMAEMA as a pH-driven “gatekeeper” realized the controlled release of BTA from microcapsules at acid conditions. The surface morphology analysis, electrochemical impedance spectroscopy (EIS), and scanning electrochemical microscopy (SECM) were performed to evaluate the self-healing performance of the composite coatings. The results showed that the combination of NIR light and pH-responsive self-healing effects endowed the coating with short healing time and prominent healing efficiency.

研究领域: 材料科学 · 腐蚀与防护
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