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Polymers · 2019 ·Vol. 11 ·期 12 ·2023 · IF 3.164

Synthesis and Characterization of Novel D-A Type Neutral Blue Electrochromic Polymers Containing Pyrrole[3-c]Pyrrole-1,4-Diketone as the Acceptor Units and the Aromatics Donor Units with Different Planar Structures

Haoguo Yue,Lingqian Kong,Bo Wang,Qing Yuan,Yan Zhang,Hongmei Du,Yunyun Dong,Jinsheng Zhao

Three soluble conjugated polymers, named BEDPP, FLDPP, and CADPP, were prepared through the Suzuki polymerized reaction, and employed benzene (BE), fluorene (FL), and carbazole (CA) as the donor units, respectively. The electron-deficient molecule 2,5-bis-(2-octyldodecyl)-3,6-bis-(5-bromo-thiophene)-pyrrole[3-c]pyrrole-1,4-diketone(DPP) was introduced and used as the acceptor unit. The properties of these three copolymers were studied by a series of detailed characterization analysis, including X-ray photoelectron spectroscopy (XPS), colorimetry, electrochemical measurements, spectroelectrochemistry, kinetics, quantitative calculation, and thermogravimetric (TG) analysis, etc. The results revealed that BEDPP displayed a blue color in the neutral state and a light brown color in the oxidized state, FLDPP exhibited a cyan color in the neutral state and a gray color in the oxidized state, while CADPP displayed pure blue color in the neutral state and a light gray color in the oxidized state. All these polymers possess narrow optical band gaps lower than 1.80 eV and satisfactory thermal stability. The kinetic characterization showed that the optical contrasts (ΔT%) in the near-infrared region were superior to the visible region. The optical contrasts of BEDPP, FLDPP, and CADPP are 41.32%, 42.39%, and 45.95% in the near-infrared region, respectively, which made them a good application prospect in the near-infrared region. Amid the three polymers, CADPP has the highest coloration efficiency (around about 288 cm2·C−1) and fast switching times (0.77 s in the coloring process and 0.52 s in the bleaching process) in the visible region, and the comprehensive performance of CADPP can be comparable to that of the reported D-A (Donor-Acceptor) type blue color polymers. In general, based on the good performances and the stable neutral blue color, the three polymers had profound theoretical significance for the development of electrochromic material and the completion of the RGB (Red, Green, Blue) color space.Keywords:electrochromic;pyrrole[3-c]pyrrole-1,4-diketone;donor-acceptor;neutral blue color;conjugated polymer

研究领域: 材料科学 · 化学
✓ 已验证 DOI PubMed 高影响因子
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APPLIED SURFACE SCIENCE · 2019 · IF 5.155

Pyrene-alt-dibenzothiophene-S,S-dioxide copolymers for highly efficient photocatalytic hydrogen production: The role of linking pattern

Chang Cheng,Xunchang Wang,Feng Wang

Two analogous positional polymers P16PySO and P27PySO have been synthesized via the copolymerization from dibenzothiophene-S,S-dioxide and pyrene building blocks. The effect of the linking pattern on the molecular packing, photophysical and photocatalytic properties of the two isomers was investigated. It was interestingly found that a minor change at the substitution position of pyrene unit was demonstrated to largely influence the photocatalytic properties of the two isomers. P16PySO exhibited an encouraging average hydrogen evolution rate (HER) of 619.5 μmol h −1 and the maximum HER of 774 μmol h −1 , much higher than that of 2,7-counterpart with a moderate rate of 282 μmol h −1 . The increased photocatalytic activity of P16PySO is mainly ascribed to its more ordered molecular packing, broader absorption region, better wettability , and higher photo-generated charge mobilities. Moreover, the optimum HER was increased from 774 to 1013 μmol h −1 when the amount of the photocatalyst P16PySO was increased from 50 to 100 mg, which is among the top solar-to‑hydrogen conversion efficiencies reported so far for the polymeric photocatalysts.

研究领域: 材料科学 · 化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Efficient Total Synthesis and Herbicidal Activity of 3-Acyltetramic Acids: Endogenous Abscisic Acid Synthesis Regulators

Xiankun Liu,Shiqiang Wen,Weichen You,Xiaofei Wang,Qing X. Li,Qiang Bian,Pei Lv,Rimao Hua

An efficient synthesis method will allow a large number of tetramic acid analogues to be synthesized for property and potency optimization. In this study, a facile and efficient method was described for the synthesis of 3-acyltetramic acids. The synthesis was accomplished mainly via (1) mild intramolecular cyclization and (2) the formation of β-ketoamides between nucleophiles and acyl Meldrum’s acids. 3-Acyltetramic acid exhibited phytotoxicity against Echinochloa crusgalli and Portulaca oleracea. At a dosage of 750 g ha–1, 6k and 6a showed high herbicidal activity against E. crusgalli, Digitaria sanguinalis and P. oleracea, Amaranthus retroflexus, respectively. 6k inhibited the synthesis of endogenous abscisic acid, thus seedling germination and plant growth. The incorporation of various acyl Meldrum’s acids and amino acid esters was applicable to the parallel synthesis of 3-acyltetramic acids. The mode of action and herbicidal activity indicate that 3-tetramic acid had good herbicidal performance and was a promising herbicide candidate. This study will provide a reference for novel herbicide development.

研究领域: 化学 · 农业科学 · 植物生理学
✓ 已验证 DOI PubMed 高影响因子
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FEBS Open Bio · 2024 · IF 2.8

2-dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione mediates the effect of ROS-enhanced PI3K/Akt/mTOR pathway on autophagy in breast cancer

Linqian Chen,Meifeng Chen,Yan Xie,Yuyan Zhang,Shutian Mo,Yongfei He,Tianyi Liang,Yuan Liao,Renbin Huang,Guodong Huang,Chuangye Han,Thi Thai Hoa Pham

Several studies have suggested a potential antitumor effect of 2-dodecyl-6-methoxycyclohexa-2,5-diene-1,4-dione (DMDD). To further understand the mechanism of action of this compound, we investigated its effect on the phosphatidylinositol-3-kinase (PI3K)/serine–threonine kinase (Akt)/mammalian target of rapamycin (mTOR) signaling pathway. We show that DMDD application significantly inhibited the proliferation of breast cancer cell lines MDA-MB-231 and ER-α positive MCF-7. Furthermore, DMDD application resulted in increased intracellular reactive oxygen species (ROS) levels, apoptosis and autophagy, whereas it downregulated the expression of PI3K, Akt and mTOR mRNA and proteins, and increased the expression of LC3II/I and p62 proteins. In a mouse breast cancer xenograft model, DMDD inhibited tumor growth. Expression analyses suggest that ROS levels were higher in DMDD treated tumor tissues, whereas immunohistochemical analyses suggest that apoptotic cells were more prevalent in the DMDD treated group compared to the control group. Taken together, our results suggest that the molecular mechanism of action of DMDD may involve the enhancement of breast cancer autophagy through the PI3K/Akt/mTOR signaling pathway by mediating ROS expression.

CAS / MDL: 589-41-3 33069-62-4
研究领域: 肿瘤学 · 细胞生物学 · 药理学 · 癌症研究
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Polymers · 2022 ·Vol. 14 ·期 18 ·3904 · IF 4.967

Synthesis and Characterization of a Self-Polycondensation Diazaphthalanone Monomer and Its Polymers from Polycondensation Reactions

Xin Liu,Xiaozhou Zhang,Jiawei Jiang,Hongge Jia,Xigao Jian,Jinyan Wang

Polyether ketone (PEK) plastics are linear thermoplastic polymers connected by at least one ether bond and at least one ketone bond on the aryl group. The reason for their excellent heat resistance, rigidity, and mechanical strength is that their main molecular chain contains plenty of aromatic rings and polar carbonyl groups, and their molecular chain presents a large rigidity and strong intermolecular force. In addition, the main chain contains a considerable number of ether bonds, resulting in a certain toughness. However, polyether ketone materials have the disadvantage of poor solubility because of their excellent rigidity. To improve the solubility of polyether ketone, the preparation method of a novel nitrogenous heterocyclic polyaromatic ether monomer, 2-(4-chlorophenyl)-2,3-dihydrophthalazine-1,4-dione (CDD), was proposed, and its activity of polymerization was studied. The average molecular weight of the poly(aryl ether ketone) containing a nitrogenous heterocyclic polyaromatic ether group obtained by self-polycondensation of CDD was 4.181 × 103kg/mol, and the yield was 90.5%. In order to further explore the activity of monomers, novel copolymerized poly(aryl ether ketone) (PBCD) containing a nitrogenous heterocyclic polyaromatic ether structure was prepared by ternary copolymerization with 4,4-difluorobenzophenone (DFBP) and bisphenol fluorene (BHPF) with high activity. The average molecular weight of PBCD was 72.793 × 103kg/mol, the molecular weight distribution was 2.344, and the yield was 88.1%. Fourier transform infrared spectroscopy (FT-IR) and1H NMR were used to confirm the structure of the obtained polymer. Through thermogravimetric analysis (TGA), the determined weight loss temperature of 5% under nitrogen was higher than 500 °C, indicating excellent thermal stability. Compared with the solubility of the binary copolymer containing fluorenyl poly(aryl ether ketone) (PBD), the polymer showed reasonable solubility in selective solvents such as chloroform andN,N-dimethylacetamide.Keywords:poly(aryl ether ketone);solubility;thermal properties

CAS / MDL: 3236-71-3 345-92-6
研究领域: 高分子科学 · 材料科学 · 化学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Experimental and Therapeutic Medicine · 2020 ·Vol. 20 ·期 5 ·1-1 · IF 1.785

The compound 2‑benzylthio‑5,8‑dimethoxynaphthalene‑1,4‑dione leads to apoptotic cell death by increasing the cellular reactive oxygen species levels in Ras‑mutated liver cancer cells

Gui-Nan Shen,Jing Li,Ying-Hua Jin,Hu-Nan Sun,Ying-Ying Hao,Mei-Hua Jin,Ren Liu,Wei-Long Li,Yong-Qing Zhang,Jia-Bin Yu,Nan-Nan Yu,Wei-Dong Wang,Li-Yun Yu,Ji-Su Kim,Taeho Kwon,Ying-Hao Han

The aim of the present study was to verify the pro‑apoptotic anticancer potential of several 5,8‑dimethoxy‑1,4‑phthoquinone (DMNQ) derivatives in Ras‑mediated tumorigenesis. MTT assays were used to detect cellular viability and flow cytometry was performed to assess intracellular reactive oxygen species (ROS) levels and apoptosis. The expression levels of proteins were detected via western blotting. Among the 12 newly synthesized DMNQ derivatives, 2‑benzylthio‑5,8‑dimethoxynaphthalene‑1,4‑dione (BZNQ; component #1) significantly reduced cell viability both in mouse NIH3T3 embryonic fibroblasts cells (NC) and H‑RasG12V transfected mouse NIH3T3 embryonic fibroblasts cells (NR). Moreover, BZNQ resulted in increased cytotoxic sensitivity in Ras‑mutant transfected cells. Furthermore, the reactive oxygen species (ROS) levels in H‑RasG12V transfected HepG2 liver cancer cells (HR) were significantly higher compared with the levels in HepG2 liver cancer cells (HC) following BZNQ treatment, which further resulted in increased cellular apoptosis. Eliminating cellular ROS using an ROS scavenger N‑acetyl‑L‑cysteine markedly reversed BZNQ‑induced cellular ROS accumulation and cell apoptosis in HC and HR cells. Western blotting results revealed that BZNQ significantly downregulated H‑Ras protein expression and inhibited the Ras‑mediated downstream signaling pathways such as protein kinase B, extracellular signal‑related kinase and glycogen synthase kinase phosphorylation and β‑catenin protein expression. These results indicated that the novel DMNQ derivative BZNQ may be a therapeutic drug for Ras‑mediated liver tumorigenesis. The results of the current study suggest that BZNQ exerts its effect by downregulating H‑Ras protein expression and Ras‑mediated signaling pathways.

CAS / MDL: 937-14-4
研究领域: 肿瘤学 · 药理学 · 细胞生物学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOOD CHEMISTRY · 2023 · IF 8.8

Photoelectrochemical sensor for the detection of Escherichia coli O157:H7 based on TPA-NO2 and dual-functional polythiophene films

Xiaoqing Wang,Huiyi Chen,Jihui Zhang,Hong Zhou,Xiangying Meng,Na Wang,Yishan Fang,Bo Cui

The detection of Escherichia coli ( E. coli ) is of great significance for the environment and human health. Herein, a photoelectrochemical (PEC) detection strategy based on molecularly imprinted polymers (MIPs) was proposed for the sensitive detection of E. coli . 4,4′,4″-Trinitrotriphenylamine (TPA-NO 2 ) was prepared using a simple nitration reaction. Subsequently, MIP films were polymerized on the surface of TPA-NO 2 using 1,3-dihydrothieno[3,2- d ]pyrimidine-2,4-dione as the functional monomer with the dual functions of specific recognition and sensitization. The linear range was 10–10 8 CFU/mL and the limit of detection was 10 CFU/mL. It showed favorable recoveries in real sample tests of milk, orange juice and tomato. Additionally, the ability of functional monomers to bind excellently with E. coli was verified using molecular docking techniques. This research provided broader possibilities for constructing MIPs-PEC sensors and analyzing the interaction mechanism between E. coli and functional monomers.

研究领域: 分析化学 · 生物技术 · 环境科学 · 食品科学
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