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ACS Applied Polymer Materials · 2024 · IF 4.4

Highly Rigid and Functional Polyimides Based on Noncoplanar Benzimidazolone Diamines and Their Photolithography Application

Haiqing Zhu,Yumiao Su,Junfeng Li,Yulin Ding,Minyu Li,Wenmu Li

It is of significance to develop a photosensitive polyimide for the demand of further integration and miniaturization of integrated circuits. In the current work, the rigid benzimidazolone-derived diamines and the corresponding photosensitive polyhydroxyimide were successfully developed. All polyimides exhibit excellent processability and comprehensive physical properties. Especially, our fluorinated polyhydroxyimide has all the desirable properties for a patterning process which includes high glass transition temperature (369 °C), low dielectric constant (2.94 at 1 MHz), and excellent optical transparency (λcutoff as low as 332 nm). Based on this fluorinated polyhydroxyimide, our photosensitive polyimide has a sensitivity of 172 mJ cm–2 and a contrast of 4.2, and fine positive patterns with resolutions of 5 and 10 μm were achieved. This provides a feasible framework for expanding the application of benzimidazolone polyimide.

研究领域: 材料科学 · 电子工程
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HIGH PERFORMANCE POLYMERS · 2014 · IF 1.09

Synthesis of N-substituted poly(benzimidazole ketone ketone)s containing pyridine rings

Yewei Xu,Yi Sun,Yonglin Lei,Jichuan Huo,Lin Zhang

Poly(N-arylenebenzimidazole ketone ketone pyridine)s have been prepared via N–C coupling reaction that removed the N–H sites from the novel bis(benzimidazoyl) derivatives with activated aromatic difluorides in sulfolane. The reaction was carried out at 210°C in the presence of anhydrous potassium carbonate. The structures of the polymers were characterized by means of Fourier transform infrared and proton nuclear magnetic resonance spectroscopies and elemental analysis. All resulting polymers showed essentially amorphous patterns. Differential scanning calorimetry and thermogravimetric measurements showed that the polymers had high glass transition temperatures (>179°C), good thermostability, and high decomposition temperatures (>401°C). These novel polymers also showed easy solubility.

研究领域: 高分子化学 · 材料科学
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JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS · 2024 · IF 2.7

Design, synthesis, in-vitro biological profiling and molecular docking of some novel oxazolones and imidazolones exhibiting good inhibitory potential against acetylcholine esterase

Iqra Saleem Naz Babari,Muhammad Islam,Hamid Saeed,Humaira Nadeem,Fariha Imtiaz,Awais Ali,Nusrat Shafiq,Abdulaziz Alamri,Rabia Zahid,Imran Ahmad

Heterocyclic compounds with oxazole and imidazole rings in their structure have disclosed momentous biological aptitudes. Taking into account their superlative attributes, the present study was designed to introduce a new synthetic scheme to make new derivatives with tremendous futuristic pharmacological potentialities. Series of Oxazolones were synthesized by using substituted benzaldehyde with benzyl halides to produce respective benzaldehyde derivatives 1 (a–d) which further reacted with hippuric acid to yield oxazolones 2 (a–e). Newly synthesized oxazolones then reacted with 4-chloroaniline to yield corresponding imidazolones 3 (a–e). All the compounds were characterized by using FTIR and NMR spectroscopic techniques. Docking studies of Compounds were conducted using AutoDock Vina and analyzed with PYMOL. All synthesized oxazolone and imidazolone derivatives exhibited antioxidant potential, demonstrated by their IC50 values compared to ascorbic acid standard. Oxazolone derivatives (2a–2e) exhibited good acetyl cholinesterase inhibitory potential whereas Imidazolone series did not show significant inhibition as shown by their IC50 values compared to donepezil as a standard. Docking studies of all compounds against acetylcholinesterase demonstrated favorable binding affinity, indicating their potential for further in-vivo studies. It is notable that novel compounds of both oxazolones and Imidazolone series exhibited antioxidant potential with maximum percentage inhibition of 75.9 (IC50 12.9 ± 0.0573 µM/mL) by compound 2d while compound 2a showed AChE inhibitory potential with maximum %age inhibition of 75.49 (IC50 7.8 ± 0.0218 µM/mL).Communicated by Ramaswamy H. Sarma

CAS / MDL: 69-78-3
研究领域: 药物化学 · 药理学 · 生物化学
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MACROMOLECULAR RESEARCH · 2012 ·Vol. 21 ·期 6 ·681-686 · IF 1.153

Synthesis and characterization of poly(N-arylenebenzimidazole ketone ketone)s

Xu Yewei,Tang Jie,Chang Guanjun,Zhu Fanghua,Luo Xuan,Zhang Lin

Poly( N -arylenebenzimidazole ketone ketone)s (PNABIKKs) consisting of m - and p -phenylene linkages have been synthesized by nucleophilic aromatic substitution from bis(benzimidazolyl) derivatives containing sulfonyl, carbonyl, and ether groups with activated aromatic difluorides in sulfolane at 210 °C in the presence of anhydrous potassium carbonate. The structures of the polymers were characterized by means of Fourier tramsfom infrared (FTIR), proton nuclear magnetic resonance ( 1 H NMR) spectroscopy, and elemental analysis, and the results were largely consistent with the proposed structure. Differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) measurements demonstrated that polymers had high glass transition temperatures ( T g >220 °C) and good thermal stability with high decomposition temperatures ( T D >480 °C). These novel polymers also showed good solubility.

研究领域: 高分子化学 · 材料科学
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Journal of CO2 Utilization · 2018 · IF 5.503

The simple system of fixing CO2 to synthesize benzimidazolones at atmospheric pressure

Xianting Cao,Haizhen A. Zhong,Pengfei Zhang,Hui Zheng

A simple chemical fixation of CO 2 at atmospheric pressure to make valuable benzimidazolones derivates via the o -phenylene-diamines carbonylation reaction catalyzed by DBU/S was developed. Different reaction conditions were examined and optimized. A series of benzimidazolones derivatives were synthesized using NMP as solvent at 413K with excellent yields (80–94%). Various substrates were employed and the results suggested the wide application of our method. The quantum mechanics calculations demonstrated that the complexation of DBU with sulfur significantly enhanced the reaction. This protocol rovides a novel approach of fixing CO 2 at atmospheric pressure into a series of 2-benzimidazolones derivates.

CAS / MDL: 6674-22-2
研究领域: 有机化学 · 环境科学
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JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY · 2019 · IF 4.027

Design, synthesis, in vitro and in vivo evaluation of benzylpiperidine-linked 1,3-dimethylbenzimidazolinones as cholinesterase inhibitors against Alzheimer’s disease

Jun Mo,Tingkai Chen,Hongyu Yang,Yan Guo,Qi Li,Yuting Qiao,Hongzhi Lin,Feng Feng,Wenyuan Liu,Yao Chen,Zongliang Liu,Haopeng Sun

Cholinesterase inhibitor plays an important role in the treatment of patients with Alzheimer’s disease (AD). Herein, we report the medicinal chemistry efforts leading to a new series of 1,3-dimethylbenzimidazolinone derivatives. Among the synthesised compounds, 15b and 15j showed submicromolar IC50 values (15b, eeAChE IC50 = 0.39 ± 0.11 µM; 15j, eqBChE IC50 = 0.16 ± 0.04 µM) towards acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Kinetic and molecular modelling studies revealed that 15b and 15j act in a competitive manner. 15b and 15j showed neuroprotective effect against H2O2-induced oxidative damage on PC12 cells. This effect was further supported by their antioxidant activity determined in a DPPH assay in vitro. Morris water maze test confirmed the memory amelioration effect of the two compounds in a scopolamine-induced mouse model. Moreover, the hepatotoxicity of 15b and 15j was lower than tacrine. In summary, these data suggest 15b and 15j are promising multifunctional agents against AD.

研究领域: 药理学 · 神经科学 · 药物化学
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POLYHEDRON · 2025 · IF 2.6

A hydrogen-bonded organic framework directed by organophosphate and 2-benzimidazolone

Chaochao Fan,Huanhuan Duan,Yue Wang,Wei Zuo,Wei Sun,Chuandong Jia

The assembly of hydrogen-bonded organic frameworks (HOFs) has been one of the focuses of supramolecular chemistry, while the HOFs based on organophosphate anion and neutral tecton have rarely been reported. Herein we utilized the emerging anion coordination-driven assembly (ACDA) strategy to successfully construct one novel two dimensional (2D) porous hydrogen-bonded organic framework ( 1 ) formed by the anion coordination of neutral and commercially available 2-benzimidazolone as hydrogen bonding donor, namely ligand L 1 , with organophosphate anion (PhOPO 3 2− ) as hydrogen bonding acceptor in a single-step crystallization. The assembly of organophosphate-directed 2D HOF was elucidated by single crystal X-ray diffraction analysis, in which the bridged water molecule played a significant role in respect of the formation of the O H⋯O hydrogen bonds and N H⋯O hydrogen bonding. Interestingly, TEA + cations were encapsulated within the aromatic cavities of the grid-like HOF mainly through C H⋯π interactions. This study is looking forward to furnishing new insights into the construction of hydrogen-bonded molecular frameworks with porosity utilizing anion coordination chemistry.

CAS / MDL: 615-16-7
研究领域: 超分子化学 · 材料科学 · 晶体工程 · 阴离子配位化学
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