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SYNTHESIS-STUTTGART · 2019 ·Vol. 52 ·期 02 ·297-303 · IF 2.867

DMSO-Mediated Synthesis of Methylene-Bridged Unsymmetrical Bisamides in the Presence of AcOH

Yi Zhang,Dongheng Zhou,Yongmin Ma,Jing Chen

A simple and efficient procedure for the synthesis of N-[(methylthio)methyl]benzamides and methylene-bridged unsymmetrical bisamides was achieved mediated by DMSO in the presence of acetic acid. DMSO plays a dual role in the transformation, as not only a solvent, but also an environmentally benign methylene source. The protocol provides new strategies for effective synthesis of unsymmetrical bisamides and avoids the use of transition-metal catalysts.

研究领域: 有机化学 · 绿色化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF POLYMER SCIENCE · 2024 · IF 3.9

Synthesis of colorless polyimides derived from benzimidazole diamines with bis-amide structures

Hao Zhang,Feng Guo,Ke Xu,Mengxia Wang,Chunhai Chen,Guangtao Qian,Gang Liu,Zhiqing Deng

To make the colorless polyimides (CPIs) suitable for the application of flexible display technology, the polyimide (PI) films need to have both good optical properties and thermal properties. To get the wanted properties, 2-(2-methyl-4-(2-methyl-4-aminobenzamido)phenyl)-5-(2-methyl-4-aminobenzamido)- N -phenylbenzimidazol (5a) and 2-(2-methyl-4-(2-trifluoromethyl-4-aminobenzamido)phenyl)-5-(2-trifluoromethyl-4-aminobenzamido)- N -phenylbenzimidazol (5b) were synthesized, which both contained benzimidazole and bis-amide structures. Two kinds of PI films were polymerized with cyclobutane-1,2,3,4-tetracarboxylic dianhydride (CBDA). With the contribution of side groups (  CH 3 or  CF 3 ), the resulting PI films presented relatively superior optical properties (transmittance at 400 nm was 59% and 68% respectively) and low coefficient of thermal expansion (CTE = 22 and 25 ppm K −1 ). These good properties suggest that these PI films have the potential for flexible display usage. Graphical

研究领域: 材料科学 · 化学工程
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HIGH PERFORMANCE POLYMERS · 2024 · IF 1.8

Polyimides with ultra-low coefficient of thermal expansion derived from diamine containing bisbenzimidazole and bisamide

Chuyi Fang,Ke Xu,Tao Li,Guangtao Qian,Dandan Li,Chunhai Chen

To provide polyimide (PI) with high heat resistance and ultra-low coefficient of thermal expansion (CTE) for use in flexible display substrates, a novel diamine with bisbenzimidazole and bisamide groups, namely N,N'-(1H,1'H-[5,5'-bibenzo[d]imidazole]-2,2'-diyl)bis(4-aminobenzamide) (BZBA), was designed and successfully synthesized. Several poly(benzimidazole-amide-imide) (PBIAI) films were prepared by thermal imidization with 3,3',4,4'-biphenyltetracarboxylic dianhydride (BPDA), 4,4'-oxydiphthalic anhydride (ODPA), 3,3',4,4'-benzophenonetetracarboxylic dianhydride (BTDA), and 4,4'-(hexafluoroisopropylindene)-diphthalic anhydride (6FDA), respectively. Among them, BZBA-BPDA has a high glass transition temperatures (Tg = 345 °C) while achieving an extremely low coefficients of thermal expansion (CTE = 1.9 ppm K−1), meeting the processing requirements of polymer flexible substrates in OLED devices. The effects of different dianhydrides on the performance of PBIAIs were compared, providing a meaningful reference for further adjusting the PI molecular structure to meet specific requirements for industrial polymer films.

研究领域: 材料科学 · 高分子化学
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Journal of Inorganic and Organometallic Polymers and Materials · 2016 ·Vol. 27 ·期 1 ·176-185 · IF 1.308

Hydrogen Bonding Interactions Directed Various Supramolecular Networks Based on Octamolybdates and Different Flexible Bis-Pyridyl-Bis-Amide Ligands

Sun Junjun,Lin Hongyan,Chang Zhihan,Wang Xiuli,Liu Guocheng

Four new inorganic–organic hybrid supramolecular architectures constructed from octamolybdates (Mo 8 O 26 ) and different bis-pyridyl-bis-amide ligands, (3-dpye = N,N ′-bis(3-pyridinecarboxamide)-1,2-ethane, 4-dpye = N,N ′-bis(4-pyridinecarboxamide)-1,2-ethane, 3-dpyp = N,N ′-bis(3-pyridinecarboxamide)-1,3-propane, 4-dpyp = N,N ′-bis(4-pyridinecarboxamide)-1,3-propane): (3-H 2 dpye)(γ-Mo 8 O 26 ) 0.5 ( 1 ) and (4-H 2 dpye)[(4-dpye)(γ-Mo 8 O 26 )] 0.5 ·2H 2 O ( 2 ) and [(3-H 2 dpyp) 2 (β-Mo 8 O 26 )]·2H 2 O ( 3 ) [(4-H 2 dpyp) 2 (β-Mo 8 O 26 )]·2H 2 O ( 4 ), have been hydrothermally prepared and structurally characterized by single crystal X-ray diffraction analyses. Compound 1 exhibits a 3D 6-connected supramolecular framework assembled from 1D γ-Mo 8 O 26 inorganic chains and 3-H 2 dpye molecules. Compound 2 consists of an uncommon 1D γ-Mo 8 O 26 –4-dpye inorganic–organic hybrid chain connected by Mo–N bond, which are extended by 4-H 2 dpye molecules to a 3D 3,8-connected supramolecular framework. Compounds 3 and 4 show 3D 6,6-connected supramolecular framework and 2D 3,6-connected supramolecular layer based on β-Mo 8 O 26 anions and 3/4-H 2 dpyp molecules via hydrogen bonds, respectively. The different bis-pyridyl-bis-amide ligands, isomers of octamolybdates and hydrogen bonding interactions in the title compounds show great effects on the final supramolecular networks. The electrochemical, electrocatalytic and photocatalytic activities of compounds 1–4 have been investigated.

研究领域: 无机化学 · 材料科学
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MICROCHIMICA ACTA · 2024 ·Vol. 192 ·期 1 ·1-12 · IF 5.3

Covalent organic frameworks hybridized polymeric high internal phase emulsions with amphiphilicity for extraction of trace bisamide insecticides in food samples

Su Lin,Wu Zhuqiang,Ruan Guihua,Huang Yipeng

Polymeric high internal phase emulsions decorated with covalent organic frameworks (polyHIPEs-COFs) were synthesized and used as the sorbent for cyantraniliprole and chlorantraniliprole. Pickering high internal phase emulsions stabilized by covalent organic frameworks solid particles and liquid surfactants (Span80 and polyvinylpyrrolidone) endow the composites with open-cell structures and superwettability. The amphiphilicity and open-cell structures enable rapid adsorption and desorption for cyantraniliprole and chlorantraniliprole, and the solid-phase extraction process can be completed in 5 min. The adsorption efficiencies of polyHIPEs-COFs for cyantraniliprole and chlorantraniliprole are above 85.19%, but lower than 10% for fenvalerate, anti-aphid, and chlorpyrifos, demonstrating the good adsorption selectivity for cyantraniliprole and chlorantraniliprole. The adsorption efficiencies of cyantraniliprole and chlorantraniliprole using a same polyHIPEs-COFs and five different batches of polyHIPEs-COFs range from 94.25 to 100.00%, revealing the good reproducibility of the sorbent. In addition, the polyHIPEs-COF-based solid-phase extraction combined with high-performance liquid chromatography-ultraviolet detector (HPLC–UV) was developed for determination of bisamide insecticides in vegetable (eggplants, tomatoes, and peppers) samples. Results showed that the method was feasible to determine the cyantraniliprole and chlorantraniliprole in real vegetable samples with a linear range of 0.012–1.2 μg/kg and limits of detection of 0.0075–0.0090 μg/kg. The recoveries of cyantraniliprole and chlorantraniliprole spiked in vegetable samples ranged from 85.00 to 100.00% with relative standard deviations less than 3.52%. The study indicates the feasibility of amphiphilic polyHIPEs-COFs in extraction and enrichment of bisamide insecticides from vegetable samples for HPLC–UV analysis. Graphical

研究领域: 分析化学 · 食品科学
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JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY · 2024 · IF 1.3

Design, Synthesis and Biological Activities of Novel meta-Diamide Compounds Containing 1,2,4-Oxadiazole Group

Huang Pengmian,Yang Ting,Liu Jiyong,Xiang Juncheng,Wu Minghui

To discover new bisamide compounds with insecticidal and fungicidal activities, 19 novel cyproflanilide derivatives containing 1,2,4-oxadiazole group were designed and synthesized according to the principle of biologically active factor splicing. Preliminary biological assay data indicated that the majority of target compounds demonstrated significant insecticidal activity against Lepidopteran pests. Meanwhile, compounds 5p and 5q showed 97.22 and 100% lethality against Tetranychus cinnabarinus at 400 mg L-1, which were better than cyproflanilide (41.11% at 400 mg L-1). In addition, it is exciting that we have achieved our initial goals as some of the target compounds exhibited both insecticidal and fungicidal activities. For instance, compounds 5b and 5c showed 59.26 and 74.07% fungicidal activities against Cucumber downy mildew at 400 mg L-1, as well as 100% insecticidal activity against Plutella xylostella and armyworm at 100 mg L-1. Compound 5h showed 100% insecticidal activity against armyworm at 10 mg L-1, and also displayed 66.67% fungicidal activity against Cucumber downy mildew at 400 mg L-1. The inhibition rate of compounds 5l and 5s against Cucumber downy mildew reached 88.89 and 96.30% at 400 mg L-1. This work showed the effectively fungicidal application of 1,2,4-oxadiazole group in bisamide compounds and provides insights for optimal structural design.

研究领域: 农药化学 · 有机合成 · 植物保护
✓ 已验证 DOI 高影响因子
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Frontiers in Chemistry · 2022 · IF 5.545

Design, synthesis, and insecticidal activity evaluation of piperine derivatives

Zhang Chiying,Tian Qingqiang,Li Yahui

Structural optimization of natural products has become one of the most effective ways to develop novel pesticides. In this study, 30 novel pesticide derivatives containing a linear bisamide were synthesized. Then, their insecticidal activities against P. xylostella were evaluated. Results indicate that different bisamide substitutes show different larvicidal structure–activity relationships. At the same time, 2-trifluoroethyl is the most efficient substituent. The bioactivity results showed that most of the desired compounds exhibited better insecticidal activity against P. xylostella than piperine. Among them, compound D28 resulted in 90% mortality at 1 mg/ml concentration. This study provides a novel protocol for the discovery of new insecticides. The molecular docking results indicated that compound D28 could act on γ-aminobutyric acid receptors.

研究领域: 农药化学 · 分子生物学
✓ 已验证 DOI 高影响因子
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JOURNAL OF SOLID STATE CHEMISTRY · 2017 · IF 2.299

Four thiophene-pyridyl-amide-based ZnII/CdII coordination polymers: Assembly, structures, photocatalytic properties and fluorescent recognition for Fe3+

Xiu-Li Wang,Xiao-Mei Wu,Guo-Cheng Liu,Qiao-Min Li,Hong-Yan Lin,Xiang Wang

By tuning metal ions and combining with different dicarboxylates , four new semi-rigid thiophene-bis-pyridyl-bis-amide-based coordination polymers , namely, [Zn(3-bptpa)(1,3-BDC)]·DMA·2H 2 O ( 1 ), [Zn(3-bptpa)(5-MIP)] ( 2 ), [Cd(3-bptpa)(1,3-BDC)]·2H 2 O ( 3 ) and [Cd(3-bptpa)(5-MIP)]·4H 2 O ( 4 ) (3-bptpa= N,N′ -bis(pyridine-3-yl)thiophene-2,5-dicarboxamide, 1,3-H 2 BDC=1,3-benzenedicarboxylic acid, 5-H 2 MIP=5-methylisophthalic acid, DMA= N,N -dimethylacetamide), were solvothermally/hydrothermally synthesized and structurally characterized by single-crystal X-ray diffraction analyses, IR spectra , UV–vis diffuse-reflectance spectra (DRS), powder X-ray diffraction (PXRD) and thermal gravimetric analyses (TG). The structural analysis reveals that Zn-complexes 1 and 2 are similar 2D networks. While Cd-complexes 3 and 4 exhibit similar 2-fold interpenetrating 3D α -Po frameworks with the (4 12 ·6 3 ) topology. The photocatalytic properties for the degradation of methylene blue (MB) under ultraviolet light irradiation of the title complexes have been investigated in detail. Furthermore, the luminescent sensing behaviors for metal cations of 1–4 have been studied, the results indicate that 3 is an excellent fluorescent probe , with high sensitivity, selectivity , and simple regeneration, for environmentally relevant Fe 3+ ions.

研究领域: 无机化学 · 材料化学 · 配位化学 · 环境分析 · 光催化 · 荧光传感
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RESEARCH ON CHEMICAL INTERMEDIATES · 2017 ·Vol. 43 ·期 11 ·6115-6130 · IF 1.369

Synthesis of novel 1,3,4-oxadiazole derivatives containing diamides as promising antibacterial and antiviral agents

Wang Pei-Yi,Shao Wu-Bin,Xue Hai-Tao,Fang He-Shu,Zhou Jian,Wu Zhi-Bing,Song Bao-An,Yang Song

In this paper, a variety of novel 1,3,4-oxadiazole derivatives possessing diamides were synthesized and tested for their antibacterial and antiviral activity. Preliminary antibacterial assays indicated that some intermediates and title compounds displayed excellent inhibition effects against plant pathogens Xanthomonas oryzae pv. oryzae ( Xoo ) and Xanthomonas axonopodis pv . citri ( Xac ). Further studies revealed that compound H15 exhibited the strongest activities against Xoo and Xac with minimal EC 50 values of 0.7 and 5.9 μg/mL, respectively. Antiviral bioassays suggested that some of these structures displayed appreciable curative activities and moderate protective effects against tobacco mosaic virus (TMV) in vivo. Among them, compound H8 exerted the best chemotherapeutic effect against TMV with the curative rate of 60.0% at 500 µg/mL, which was comparable with those of commercial agricultural antiviral agent ningnanmycin (54.2%). Given their significant biological activities, this kind of compound could serve as new leading compounds in the study of antibacterial and antiviral chemotherapy.

研究领域: 药理学 · 植物病理学 · 有机化学
✓ 已验证 DOI 高影响因子
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2025 · IF 4.6

Systematic evaluation of three-generation diamide insecticides with glutathione reductase 2: molecular mechanisms and phytotoxic effects

Yifan Chen,Fan Yang,Xiaomin Hou

As representative compounds spanning three generations of diamide insecticides, flubendiamide, chlorantraniliprole, and tetraniliprole have been extensively employed in agricultural practices. However, their widespread application induces oxidative stress in plants and underlying toxic mechanisms remain poorly understood. Given the important roles in oxidative stress, glutathione reductase 2 from Arabidopsis thaliana ( At GR2) was applied as a biomarker to evaluate the toxicological effects of diamide insecticides. Firstly, the root elongation in Arabidopsis seedlings was significantly inhibited and the At GR2 gene expression level was up-regulated under exposure of the diamide insecticides. Then the glutathione reductase activity of At GR2 was decreased with the increase concentration of these three insecticides, especially for flubendiamide with similar detrimental effects at much lower concentrations. Moreover, the binding affinity between flubendiamide and At GR2 was also stronger than that of chlorantraniliprole and tetraniliprole, which was conformed with molecular docking results. Additionally, much more evident effects on the structure of At GR2 under exposure of flubendiamide was detected through multispectral techniques compared to the other two insecticides. Hence this study systematically explored the binding mechanism of these three-generations of diamide insecticides with At GR2 at the molecular level, and further provided critical assessments of their phytotoxic effects on plant development and agricultural systems.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF CHROMATOGRAPHY A · 2019 · IF 3.858

Preparation of a stilbene diamido-bridged bis(β-cyclodextrin)-bonded chiral stationary phase for enantioseparations of drugs and pesticides by high performance liquid chromatography

Yazhou Shuang,Tianci Zhang,Laisheng Li

A stilbene diamido-bridged bis (β-cyclodextrin) was synthesized via the reaction between 4,4′-stilbene dicarboxylic acid and 6- deoxy -6-amino-β-cyclodextrin. Then it was bonded onto the surface of an ordered mesoporous SBA-15 to obtain a novel bridged bis (β-cyclodextrin)-bonded chiral stationary phase (SBCDP). The structures of the bridged bis (β-cyclodextrin) and SBCDP were characterized by the mass spectrometry, nuclear magnetic resonance, infrared spectroscopy, elemental analysis and thermogravimetric analysis. The chromatographic performance of SBCDP was systematically evaluated by separating 23 racemic drugs and pesticides, including trimeprazine, praziquantel, flavanones, β-blockers and triazole pesticides in the reversed-phase chromatography or the polar organic mode. The chromatographic conditions that affect the enantioselectivity or diasterioselectivity of SBCDP were investigated in detail, including the mobile phase composition, pH value and column temperature. As a result, all tested analytes were resolved on SBCDP with high resolutions (1.51∼5.15) within about 25 min, and the enantioseparation resolutions of flavanone and imazalil were up to 5.15 and 4.38, respectively. Compared with the native β-cyclodextrin stationary phase (CDCSP), the SBCDP had a better chromatographic performance in enantioselectivity and diasterioselectivity. For example, enantiomers of trimeprazine, praziquantel, flavanone and imazalil those could not be separated by CDCSP, were separated by SBCDP with high resolutions. Unlike the small cavity (0.65 nm) of native CD, the bridging linker of the bridged bis (β-CD) supplied a well-organized “ pseudo-cavity” , and combined two native CDs as an organic whole, which could synergistically encapsulate and complex some bulky analytes, making the chiral discrimination of SBCDP more precise. Moreover, we also found that SBCDP possessed high enantioselectivity and diastereoselectivity over a wide range of temperature (30∼60 °C), which made the fast analysis possible. As a new chiral separation material, SBCDP may have wider applications in analysis of chiral compounds.

研究领域: 分析化学 · 色谱技术
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JOURNAL OF HAZARDOUS MATERIALS · 2022 · IF 14.224

Molecularly imprinted self-buffering double network hydrogel containing bi-amidoxime functional groups for the rapid hydrolysis of organophosphates

Lan Wang,Peng Jiang,Weijie Liu,Jiaqi Li,Zhaoming Chen,Tianying Guo

The development of high-performance catalyst materials with high catalytic activity for the hydrolysis of organophosphorus toxicants without additional pH buffer conditions has become an urgent need for practical application. Here, a multifunctional molecularly imprinted polymer double network hydrogel (MIP-DN) material has been prepared by integrating the first polymer network containing the functional group of bi-amidoxime as the catalytic active center and the cationic polymer polyethyleneimine (PEI) with pH buffer function as the main component of the second network. Advantageously, the resultant MIP-DN hydrogel showed excellent catalytic performance without additional pH buffer conditions, exhibiting a half-life of 25 min for the hydrolysis of paraoxon in pure water. Together with multi-functions of high catalytic activity, self-buffering function and excellent processability, the MIP-DN hydrogel prepared in this work provides a new strategy for the preparation of catalytic materials with practical application value toward toxic organophosphates .

CAS / MDL: 78-67-1
研究领域: 材料科学 · 环境科学 · 催化 · 高分子化学
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