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吡啶鎓基
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY · 2018 ·Vol. 2018 ·期 11 ·1321-1325 · IF 2.882

A Water-Soluble [2]Biphenyl-Extended Pillar[6]arene

Jia-Rui Wu,Chun-Yu Wang,Yan-Chun Tao,Yan Wang,Chunju Li,Ying-Wei Yang

Graphical The facile synthesis of a diverse range of [2]biphenyl-extended pillar[6]arenes is described. Among the compounds generated is the first water-soluble version, bearing eight pyridinium moieties; this compound showed strong binding capabilities towards some sulfonate anion guests in aqueous solution and holds great potential for the detection or separation of anionic naphthalenesulfonates through rapid precipitation. The facile design and synthesis of a series of extended pillar[6]arene derivatives is described. In particular, the first water-soluble version bearing eight pyridinium moieties (CWBpP6) showed strong binding capabilities towards certain guest compounds with sulfonate groups. Significantly, CWBpP6 could uptake 2,6-naphthalene-disulfonate from water due to the rapid precipitation upon host–guest complexation, which indicates the potential of CWBpP6 as a promising detection and separation agent for naphthalene sulfonate substrates in water. This provides a possibility for further development of extended pillararenes in selective cargo precipitation as well as sensing and detection of analytes.

研究领域: 超分子化学 · 有机合成 · 材料科学
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ENVIRONMENTAL POLLUTION · 2024 · IF 7.6

Efficient removal of perrhenate/pertechnetate by a pyridinium-based porous polymer

Miaomiao He,Yuxuan Chen,Guangyuan Chen,Wenhao Li,Mingxing Zhang,Chao Zhang,Hao Zhang,Xingyi Long,Kui Tang,Tao Duan,Lin Zhu

The extraction of 99 TcO 4 − from radioactive effluents is extremely crucial for the purposes of nuclear disposal and environmental remediation. Herein, utilizing a facile and low-cost synthesis method, we report a pyridinium-based cationic polymer network , CPP-Cl, with impressive adsorption performance and ultrafast adsorption kinetics towards ReO 4 − . The structure featuring highly density of charged pyridinium units was synthesized, making it an effective adsorbent for capturing ReO 4 − . The material showed fast ReO 4 − adsorption kinetics reaching adsorption equilibrium within 30 s, an excellent capture capability of 1069.7 mg/g, and exceptional separation efficiency of 94.3% for removing 1000 ppm ReO 4 − . Furthermore, it possessed excellent reusability in multiple sorption/desorption trials and good uptake capacity within a widely ranging pH values. It is noteworthy that the extraction efficiency of CPP-Cl for ReO 4 − from simulated nuclear waste can be up to 94.2%. The favorable performance of the material in multiple tests revealed that CPP-Cl has tremendous potential as a high-efficiency sorbent for capturing 99 TcO 4 − /ReO 4 − in complex nuclear associated environmental systems.

研究领域: 环境科学 · 核化学 · 材料科学
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NEW JOURNAL OF CHEMISTRY · 2019 ·Vol. 43 ·期 46 ·18251-18258 · IF 3.069

Positive charge-dependent cell targeted staining and DNA detection

Pei Yin,Tao Wang,Yuan Yang,Weidong Yin,Shaoxiong Zhang,Zengming Yang,Chunxuan Qi,Hengchang Ma

The chemical structures or positive charge-guided specific cell organelles' staining was an interesting but very challenging research work. In this paper, we synthesized a series of triphenylamine (TPA) derivatives with mono-, di- and tri-pyridinium as substituent groups. By exchanging the negative ions (I−, BF4− and PF6−) between them, a platform containing small compounds was established. After that, mammalian cells of HeLa and plant cells of BY-2 were employed for the study on cell imaging. The results clearly demonstrated that mono-pyridinium derivatives (TPA-Py-I−, TPA-Py-BF4− and TPA-Py-PF6−) are mitochondrion-targeted (for HeLa cells) and cell wall-targeted (for BY-2 cells). However, both di- and tri-pyridinium substituted derivatives (TPA-diPy-BF4− and TPA-triPy-BF4−) were nucleus-targeted for both cell lines. From these important findings, we can conclude that the quantity of positive charge plays a decisive role in different cell organelle-targeted staining. We also declared that our research results were very useful for designing and synthesizing probes with good cellular uptake capability, significantly enhanced targeting ability, and DNA detection.

研究领域: 细胞生物学 · 分子生物学 · 化学
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Molecular Catalysis · 2019 · IF 2.938

Brøsted acidic pyridinium-based ILs catalyzed the selective dimerization of isobutene: Performance and in-situ NMR study

Xiaojia Yu,Ying Liu,Hui Wang,Weiguo Cheng,Youqing Wu,Suojiang Zhang

Brøsted acidic pyridinium-based ILs of [NS][CF 3 SO 3 ] and [NS][HSO 4 ] have been synthesized for oligomerization of isobutene with the excellent conversion of 92.8% and the good selective dimerization at the temperature of below 100 °C. Hydroxyl-containing materials, especially ethanol, could facilitate catalytic activities to excellent conversions of isobutene and 84.2% selectivity of diisobutene. [NS][CF 3 SO 3 ] could be recovered by a simple liquid-to-liquid separation and reused more than ten times without obvious loss of catalytic activities. The formation process of oligomers has been examined by in-situ NMR spectroscopy, and a step-by-step generation process of carbonium ions varying from C 4 + , C 8 + to C 12 + was proposed. The work behaves the significance of constructing a better catalysis system for highly selective dimerization of isobutene, and potential being scaled-up for industrialization.

CAS / MDL: 1493-13-6
研究领域: 催化化学 · 材料科学
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MOLECULAR CRYSTALS AND LIQUID CRYSTALS · 2021 · IF 0.896

Methylation driven molecular packing difference at the smectic phases of a series of pyridinium-based chiral ionic liquid crystals

Peng Zhu,Limin Wu,Wei Liu,Baozong Li,Yi Li,Yonggang Yang

A series of pyridinium-based chiral ionic liquid crystals were designed and synthesized. All of them exhibit enantiotropic smectic phases. The methylation on the pyridine ring not only decreases the melting point and clearing point, but also drives structural transitions from bilayer molecular packing structures to interdigitated monolayer ones at the smectic A and C phases. Due to entropy increase, the clearing point of the liquid crystal derived from 2-methylpyridine is higher than that derived from 3-methylpyridine, and then that derived from 4-methylpyridine.

研究领域: 材料科学 · 物理化学 · 液晶
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JOURNAL OF MOLECULAR LIQUIDS · 2021 · IF 6.165

Valorization of chitin derived N-acetyl-D-glucosamine into high valuable N-containing 3-acetamido-5-acetylfuran using pyridinium-based ionic liquids

Hongjun Zang,Jing Lou,Shuolei Jiao,Huanxin Li,Yannan Du,Jiao Wang

Chitin and its derivatives contain biologically fixed nitrogen elements, which can provide nitrogen sources for N-containing chemicals. Herein, a series of pyridinium-based ionic liquids were synthesized to directly catalyze the conversion of N -acetyl-D-glucosamine (NAG, the monomer of chitin) to 3-acetamido-5-acetylfuran (3A5AF). The yield of 3A5AF in 1-carboxymethyl pyridinium chloride ionic liquid reached 37.49%, without any additives. Using B 2 O 3 and CaCl 2 as additives, the optimum yield increased to 67.37% at 180 °C in 20 min. In addition, HPLC-MS analysis has been utilized to elucidate the reaction mechanism. This research on turning “waste” into “wealth” opens up new ways for the utilization of biomass waste, which not only reduces environmental pollution but also has potential economic value.

CAS / MDL: 7512-17-6 1398-61-4
研究领域: 化学工程 · 绿色化学 · 材料科学
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SENSORS AND ACTUATORS B-CHEMICAL · 2020 · IF 7.1

Tuning the hydrophobicity of pyridinium-based probes to realize the mitochondria-targeted photodynamic therapy and mitophagy tracking

Yuyang Zhang,Lianke Wang,Qingpeng Rao,Yingcui Bu,Tianren Xu,Xiaojiao Zhu,Jie Zhang,Yupeng Tian,Hongping Zhou

Targeting mitochondria and dynamically tracking mitophagy are profoundly important in the field of photodynamic therapy (PDT) which relies on the photosensitizers (PSs) under light irradiation. While simultaneously realizing the effective reactive oxygen species (ROS) generation, accurately mitochondrial targeting, and dynamic tracking in a single PS still is a challenging issue. In this context, a series of pyridinium-based cationic fluorogens with aggregation induced emission (AIE) has been developed for this issue. The hydrophobicity of these fluorogens can be finely tuned by modulating the length of the alkyl chains on pyridinium unit. The well-tuned hydrophobicity of TL8C with C 8 -alkyl chain gives rise to the specifically mitochondrial targeting capability of TL8C based on the appropriate synergistic effect of hydrophobic and electrostatic interaction. Meanwhile, TL8C can produce ROS in high efficiency. The excellent mitochondrial targeting and the effective ROS generation allow TL8C for the specifically mitochondria-targeted PDT as well as the real time monitoring of mitophagy.

CAS / MDL: 307554-62-7
研究领域: 生物化学 · 分子生物学 · 医学 · 细胞生物学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2020 · IF 4.192

Synthesis and Docking Study of N-(Cinnamoyl)-N′-(substituted)acryloyl Hydrazide Derivatives Containing Pyridinium Moieties as a Novel Class of Filamentous Temperature-Sensitive Protein Z Inhibitors against the Intractable Xanthomonas oryzae pv. oryzae Infections in Rice

Xiang Zhou,Yu-Mei Feng,Pu-Ying Qi,Wu-Bin Shao,Zhi-Bing Wu,Li-Wei Liu,Yi Wang,Hao-Dong Ma,Pei-Yi Wang,Zhong Li,Song Yang

Xanthomonas oryzae pv. oryzae (Xoo) is an offensive phytopathogen that can invade a wide range of plant hosts to develop bacterial diseases, including the well-known rice bacterial leaf blight. However, few agrochemicals have been identified to effectively prevent and eliminate Xoo-induced diseases. Thus, designing novel antibacterial compounds on the basis of the potential targets from Xoo may lead to the discovery of highly efficient and innovative anti-Xoo agents. Filamentous temperature-sensitive protein Z (FtsZ), an important functional protein in the progression of cell division, has been widely reported and exploited as a target for creating antibacterial drugs in the field of medicine. Therefore, the fabrication of innovative frameworks targeting XooFtsZ may be an effective method for managing bacterial leaf blight diseases via blocking the binary division and reproduction of Xoo. As such, a series of novel N-(cinnamoyl)-N′-(substituted)acryloyl hydrazide derivatives containing pyridinium moieties were designed, and the anti-Xoo activity was determined. The bioassay results showed that compound A7 had excellent anti-Xoo activity (EC50 = 0.99 mg L–1) in vitro and distinct curative activity (63.2% at 200 mg L–1) in vivo. Further studies revealed that these designed compounds were XooFtsZ inhibitors, validating by the reduced GTPase activity of recombinant XooFtsZ, the nonfilamentous XooFtsZ assembly observed in the TEM images, and the prolonged Xoo cells from the fluorescence patterns. Computational docking studies showed that compound A7 had strong interactions with ASN34, GLN193, and GLN197 residues located in the α helix regions of XooFtsZ. The present study demonstrates the developed FtsZ inhibitors can serve as agents to control Xoo-induced infections.

CAS / MDL: 140-10-3
研究领域: 植物病理学 · 分子生物学 · 药物化学
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