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LIQUID CRYSTALS · 2013 · IF 1.959

Synthesis and mesomorphic properties of 2-(4′-alkoxybiphenyl-4-yl)-1H-benzimidazole derivatives

Lina Zhang,Xinbing Chen,Fengqi Zhao,Xuezhong Fan,Pei Chen,Zhongwei An

Three series of 2-(4′-alkoxybiphenyl-4-yl)-1H-benzimidazole derivatives (nM-x), which possessed 5-nitrobenzimidazole (nM-N series), benzimidazole (nM-H series) or 5-methylbenzimidazole (nM-M series) units at the end of the molecule, were synthesised and characterised by infrared, 1H- and 13C-nuclear magnetic resonance spectra, electrospray ionisation-mass spectrometry and elemental analysis. Their phase transition behaviour was investigated by differential scanning calorimetry, polarising optical microscopy and X-ray diffraction. All the compounds exhibited enantiotropic smectic mesophases with wide temperature domains for a carbon number in the alkoxy chain from 6 to 16, where the mesophase ranges were 14–91°C and 17–99°C during heating and cooling processes for the nM-N compounds, 7–25°C and 8–49°C for the nM-H compounds and 48–81°C and 52–85°C for the nM-M compounds, respectively. The effect of the length of alkoxy chain on mesomorphic properties was discussed. The nM-N and nM-M exhibited a much wider mesophase range whether during heating or cooling process than the corresponding nM-H series, especially for the longer terminal chain (n > 8), which indicated that the substituent in the benzimidazole moiety was helpful in increasing the mesophase stability.

研究领域: 有机化学 · 材料科学
✓ 已验证 DOI 高影响因子
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APPLIED SURFACE SCIENCE · 2018 · IF 4.439

Benzimidazole grafted polybenzimidazole cross-linked membranes with excellent PA stability for high-temperature proton exchange membrane applications

Xue Tian,Shuang Wang,Jinsheng Li,Fengxiang Liu,Xu Wang,Hao Chen,Di Wang,Hongzhe Ni,Zhe Wang

Benzimidazole grafted polybenzimidazole cross-linked membranes (CPBIm-X) with outstanding phosphoric acid (PA) stability are successfully prepared. 2-chloromethyl benzimidazole (CMBelm) is grafted onto PBI mainchains and using 3-glycidoxypropyltrimethoxysilane (KH560) as a cross-linker. The benzimidazole sidechains can not only increase the basic sites but also allow the membrane to achieve higher phosphoric acid uptakes without sacrificing mechanical strength. Moreover, compared with the imidazole rings in the PBI backbone, the side chain with imidazole rings are flexible, which benefit the proton transportation and lower the activation energy. In addition, the mechanical strength of cross-linked membranes is excellent. For example, the tensile strength value of CPBIm-5 is 101.4 MPa, while that of the PBIm is 79.0 MPa. The proton conductivity is enhanced because the hydrolysis of KH560 resulting Si O Si networks structure, which can absorb more phosphoric acid. The Si O Si networks in the matrix can efficiently improve the stability of phosphoric acid (PA), the remaining weight of CPBIm-5 is 57% PA. Taking into account performance comprehensively, the weight of 5% KH560 is the optimum content. For example, the proton conductivity of CPBIm-5 is 0.092 S cm −1 at 180 °C. Compared to the pristine PBI, it is almost three-fold in proton conductivity.

CAS / MDL: 2530-83-8 121-91-5
研究领域: 材料科学 · 化学工程
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ADVANCED SYNTHESIS & CATALYSIS · 2016 ·Vol. 358 ·期 17 ·2759-2766 · IF 6.453

Iodine-Mediated Aryl C−H Amination for the Synthesis of Benzimidazoles and Pyrido[1,2-a]benzimidazoles

Zhigang Lv,Jing Liu,Wei Wei,Jie Wu,Wenquan Yu,Junbiao Chang

An intramolecular aryl C−H amination reaction has been achieved using molecular iodine as the sole oxidant for the synthesis of benzimidazole derivatives. The required substrates were readily prepared by addition or coupling of arylamines with the corresponding nitriles or aryl iodides. Iodine-mediated oxidative cyclization of these substrates in the presence of potassium carbonate (K 2 CO 3 ) as base afforded the corresponding products in moderate to good yields. The transition metal-free protocol presented here is insensitive to air and operationally simple. This versatile and eco-friendly synthetic methodology is broadly applicable to a variety of N -aryl-substituted amidines and pyridin-2-amines, and provides direct access to both 1 H -benzo[ d ]imidazole and pyrido[1,2- a ]benzimidazole derivatives from the corresponding precursors.

CAS / MDL: 67-68-5 123-91-1
研究领域: 有机化学 · 药物化学
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FOOD CHEMISTRY · 2020 · IF 6.306

Ratiometric fluorescent sensing carbendazim in fruits and vegetables via its innate fluorescence coupling with UiO-67

Yong Han,Xie He,Weixia Yang,Xueli Luo,Ying Yu,Wenzhi Tang,Tianli Yue,Zhonghong Li

A ratiometric fluorescent sensor was facilely fabricated using innate fluorescence of carbendazim (MBC) and fluorescent UiO-67 to sensitively and selectively detect MBC in food matrixes. The innate fluorescence of MBC provided a signal at 311 nm (F 311 ), and the fluorescent UiO-67 at 408 nm (F 408 ) could recognize MBC through π-π stacking inducing fluorescent quenching relied on photoelectron transfer (PET). The ratio (F 311 /F 408 ) of the fluorescence enhancement of MBC and the quenching of UiO-67 linearly responded to the MBC concentrations of 0–47.6 μmol/L with a low limit of detection (LOD) of 3.0 × 10 −3 μmol/L. The reverse response signals of the sensor enhanced the sensitivity toward MBC and presented remarkable anti-interference capability in complex matrices. The as-prepared sensor was applied to detect MBC residues in apple, cucumber and cabbage, obtaining satisfactory accuracy and precision with the recovery of 90.82–103.45% and RSDs of lower than 3.03%.

研究领域: 食品科学 · 分析化学
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MOLECULES · 2016 ·Vol. 21 ·期 11 ·1574 · IF 2.465

Synthesis and Biological Evaluation of Benzimidazole Phenylhydrazone Derivatives as Antifungal Agents against Phytopathogenic Fungi

Xing Wang,Yong-Fei Chen,Wei Yan,Ling-Ling Cao,Yong-Hao Ye

A series of benzimidazole phenylhydrazone derivatives (6a–6ai) were synthesized and characterized by1H-NMR, ESI-MS, and elemental analysis. The structure of6bwas further confirmed by single crystal X-ray diffraction as (E)-configuration. All the compounds were screened for antifungal activity againstRhizoctonia solaniandMagnaporthe oryzaeemploying a mycelium growth rate method. Compound6fexhibited significant inhibitory activity againstR. solaniandM. oryzaewith the EC50values of 1.20 and 1.85 μg/mL, respectively. In vivo testing demonstrated that6fcould effectively control the development of rice sheath blight (RSB) and rice blast (RB) caused by the above two phytopathogens. This work indicated that the compound6fwith a benzimidazole phenylhydrazone scaffold could be considered as a leading structure for the development of novel fungicides.Keywords:benzimidazole;phenylhydrazone;antifungal activity

研究领域: 植物病理学 · 药物化学
✓ 已验证 DOI PubMed 高影响因子
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ACS Nano · 2022 · IF 18.027

Folded Propeller Chiral Structures Exclusively Adaptive to Chloroform

Jianjian Zhao,Aiyou Hao,Pengyao Xing

Intramolecular folding is a strategy to construct aryl chiral compounds with applications in chiroptical materials and asymmetrical catalysts. However, beyond polarity the role of solvent in controlling the folded chirality is ambiguous. Here, we report a simple folding protocol to build chiral benzimidazole skeleton with propeller chirality, which could be adaptive to chloroform (CHCl3) with high selectivity. Benzimidazole conjugated with diamino acid arms underwent folding driven by hydrogen bonds, exhibiting propeller chirality of which handedness could be tuned by the absolute chirality of amino acids. Reversible unfolding/folding behavior was realized by heating/cooling process, giving rise to the thermomediated chiroptical switch. Among up to 32 common solvents, chloroform exclusively inverted the propeller chirality. The geometry and hydrogen bonding sites of chloroform allow rearrangement of diamino acid arms into an opposite packing propensity. The chloroform behaves as an invasive linker between diamino acid arms to replace the pristine hydrogen bonds. This work reports the fabrication of chiral aryl compounds by simple folding, which shows the adaptiveness to the chloroform. It demonstrates that not only polarity but also the active participation of solvent could change the chirality and optical activities of small folded molecules.

研究领域: 有机化学 · 材料科学 · 分子生物学
✓ 已验证 DOI 高影响因子
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WATER RESEARCH · 2025 · IF 12.4

The High pKa-Guided Defect Engineering: Improving Fluoride Removal in Actual Scenarios by Benzimidazole Modulated Metal-Organic Frameworks

Ziyi Zhao,Yanan Mi,Shili Wang,Xuedong Du,Qingrui Zhang

We firstly present a novel strategy for enhancing fluoride removal from contaminated water using defect-engineered UiO-66 (Zr-MOFs), emphasizing the crucial role of pKa in modulator selection. By utilizing modulators with varying pKa values-specifically benzimidazole (BI), benzoic acid (BA), and acetic acid (AA)-we synthesized defect-rich Act-UiO-66-M(X). The higher pKa of BI facilitated greater defect formation, resulting in significantly improved adsorption capacity and faster diffusion rates. Act-UiO-66-BI(8), modulated with BI, showed a higher intensity peak at g = 2.003 in ESR analysis, indicating more oxygen vacancies. Its fluoride adsorption capacity reached 93.59 mg F/g, nearly six times higher than commercial ZrO 2 , with rapid kinetics—evidenced by a kinetic rate constant (k int ) of 2.64 mg/g·min 0.5 and equilibrium achieved within 10 minutes. The kinetic performance was enhanced by 270% compared to raw Act-UiO-66. Furthermore, Act-UiO-66-BI(8) demonstrated high selectivity and stability in high-salinity environments, with a K d coefficient consistently exceeding 17,900 mL/g. The study highlights that selecting modulators based on pKa enhances defect formation, improving active site exposure and pore diffusion, as confirmed by DFT calculations and XPS analysis. The ability of Act-UiO-66-BI(8) to treat up to 1160 kg of wastewater per kg of adsorbent highlights its potential for large-scale water purification, showcasing a promising approach for developing high-performance MOF materials.

CAS / MDL: 64-17-5 64-19-7 64-18-6
研究领域: 环境科学 · 材料科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Asian Journal of Organic Chemistry · 2022 ·Vol. 11 ·期 8 ·e202200255 · IF 3.116

Metal-free Cascade Radical Cyclization of N-Methylacrylyl-2-phenylbenzimidazole: Construction of Aryldifluoromethylated Benzimidazole[2,1-a]iso-Quinoline-6(5H)-ketone

Zhiwei Chen,Xiaoxiao Huang,Jie Sun,Yanmin Liu,Ziwei Li

Graphical A facile and effective metal-free decarboxylative cyclization of N -methacryloyl-2-phenylbenzimidazole with arylthio (oxy) difluoroacetic acids or α , α -aryldifluoroacetic acids was proposed to prepare a series of aryldifluoromethylated benzimidazole[2,1- a ] iso -quinoline-6(5 H )-one derivatives in medium to good yields with good functional group tolerance, readily available raw materials and simple operation. In addition, experimental studies showed that the CF 2 group of arylthiodifluoroacetic acids plays a crucial role in this conversion. A facile and effective metal-free decarboxylative cyclization of N -methacryloyl-2-phenylbenzimidazole with arylthio (oxy) difluoroacetic acids or α , α -aryldifluoroacetic acids was proposed to prepare a series of aryldifluoromethylated benzimidazole[2,1- a ] iso -quinoline-6(5 H )-one derivatives in medium to good yields with good functional group tolerance, readily available raw materials and simple operation. In addition, experimental studies showed that the CF 2 group of arylthiodifluoroacetic acids plays a crucial role in this conversion.

研究领域: 有机化学 · 药物化学
✓ 已验证 DOI 高影响因子
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CHEMICAL ENGINEERING JOURNAL · 2019 · IF 8.355

Semi-aromatic copolyesters with high strength and fire safety via hydrogen bonds and π-π stacking

Yan-Peng Ni,Qi-Tian Li,Lin Chen,Wan-Shou Wu,Zi-Hao Qin,Yi Zhang,Li Chen,Xiu-Li Wang,Yu-Zhong Wang

Currently, it is still a huge challenge to prepare flame-retardant polymeric materials with excellent fire safety, high strength, good durability and processability. We here propose a H-bonding cross-linking strategy that can simultaneously endow polymers with excellent flame retardancy, non-dripping behavior and enhanced strength. In this work, a novel benzimidazole monomer, 2-(4-methoxycarbonyl-phenyl)-1H-benzimidazole-5-carboxylic acid methyl ester (PBM) has been designed as a H-bonding cross-linking monomer to prepare poly(ethylene terephthalate)-based copolyesters (PET- co -PBMs). Interestingly, along with the hydrogen bonding, the π-π stacking interactions from the benzimidazole groups also exist. Due to the formation of physical crosslinking network via hydrogen bonding and π-π stacking, the melt strength of copolyesters are greatly improved. Combining with char forming ability of benzimidazole, PET- co -PBMs display excellent fire safety. Moreover, PET- co -PBMs also exhibit higher glass transition temperature, higher mechanical strength and good processability. This work provides a promising strategy to design polymers with high strength, good processability, excellent flame retardance and anti-dripping performance.

研究领域: 材料科学 · 高分子化学
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Catalysts · 2020 ·Vol. 10 ·期 4 ·436 · IF 3.52

Activated Carbon Supported Hafnium(IV) Chloride as an Efficient, Recyclable, and Facile Removable Catalyst for Expeditious Parallel Synthesis of Benzimidazoles

Xiao-Chong Peng,Shan-Shan Gong,De-Yun Zeng,Shu-Wang Duo,Qi Sun

A highly efficient method for parallel synthesis of a diversity of 1,2-disubstituted benzimidazoles fromN-substituted phenylenediamines and aldehydes has been developed by using 10 mol% HfCl4on activated carbon (HfCl4/C) as the catalyst. The newly reported HfCl4/C catalyst not only mediated fast and clean formation of benzimidazoles but also could be easily removed from the reaction solution and reused up to eight times. Scanning electron microscope (SEM) and thermal desorption studies showed that activated carbon could reversibly adsorb and release Hf(IV) in ethanol upon cooling and heating, thereby serving as a thermal-controlled solid support.Keywords:benzimidazole;hafnium chloride;catalysis;activated carbon;parallel synthesis

研究领域: 有机化学 · 材料科学
✓ 已验证 DOI 高影响因子
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JOURNAL OF POLYMER RESEARCH · 2014 ·Vol. 21 ·期 6 ·1-8 · IF 1.897

Facile synthesis of a symmetrical diamine containing bis-benzimidazole ring and its thermally stable polyimides

Yue Zhouying,Cai Yang-Ben,Xu Shiai

A new symmetrical diamine that contains benzimidazole ring, 6,6’-bis[2-(4-aminophenyl)benzimidazole], was synthesised directly from p -aminobenzoic acid and 3,3’-diaminobenzidine via benzimidazolisation condensation. The diamine monomer was polymerised with various commercial dianhydrides by a conventional two-step polymerisation reaction to obtain the corresponding polyimides. The obtained polyimides were amorphous and could be used to produce flexible, yet tough, transparent films exhibiting excellent thermal stability with glass transition temperatures of 334 °C to 412 °C and 5 % weight loss temperatures above 540 °C in nitrogen. These polymers also demonstrated outstanding mechanical properties with a tensile strength of 177 MPa to 224 MPa and a tensile modulus of 3.5 GPa to 5.7 GPa. The excellent thermal and mechanical properties of these polyimides are most likely attributable to the rigid-rod structure and the presence of hydrogen bond between the macromolecular chains.

研究领域: 材料科学 · 化学工程
✓ 已验证 DOI 高影响因子
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LIQUID CRYSTALS · 2022 · IF 2.676

The influence of the benzimidazole-based nematic liquid crystals containing ethynyl and difluoro-substitution on mesomorphic and birefringence properties

Tong Zhang,Yuyu He,Fanghua Liang,Ran Chen,Pei Chen,Xinbing Chen,Zhongwei An

A series of benzimidazole-based liquid crystal compounds containing laterally difluoro-substituted and ethynyl linking groups, namely, 2-(4-(2-(2,3-difluoro-4-(alkoxy) phenyl)ethynyl)phenyl)-1-methyl-1 H-benzimidazolem derivatives (nPF(2,3)EPMx), are synthesised and investigated for their mesomorphic properties. These compounds mainly display enantiotropic nematic mesophases in the ranges of 32.0–44.5°C (heating process) and 50.0–64.0°C (cooling process). 10PF(2,3)EPMx exhibits lower clearing points and broader nematic phase ranges than nonfluorinated reference compound 10PEPMx, because of their slightly increased dipole moment. nPF(2,3)EPMx displays much larger theoretical birefringence (0.43–0.55) and experimental birefringence (0.42–0.53) than the common tolane-based liquid crystals, which is ascribed to its large π-conjugated molecule composed of benzene core, ethynyl linking group and benzimidazole terminated unit. The theory results of three-dimensional molecular conformations with dipole moment (µ), ratio of length to width (L/W), polarisability anisotropy (Δα) and average polarisability (Δα) calculated with density functional theory are also helpful in explaining the experimental results.

研究领域: 材料科学 · 化学
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