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CRYSTENGCOMM · 2011 ·Vol. 14 ·期 3 ·1031-1037 · IF 4.006

Synthesis and characterization of thienyl-substituted pyridinium salts for second-order nonlinear optics

Liang Li,Huijuan Cui,Zhou Yang,Xutang Tao,Xinsong Lin,Ning Ye,Huai Yang

The synthesis of a series of thienyl-substituted pyridinium salts with different counter-anions and their second-order nonlinear optical (NLO) properties are described. Kurtz powder tests revealed that, out of the twelve new pyridinium salts, four possess noncentrosymmetric structures and the maximum powder second harmonic generation (SHG) efficiency is 0.6 times of DAST. Single crystals of three new salts were successfully obtained from methanol by slow evaporation method. X-Ray studies exhibited that they crystallized in the monoclinic space groupP21/c, P21, and P21/n, respectively. (E)-4-(2-(5-(dimethylamino)thiophen-2-yl)vinyl)-1-methylpyridinium 4-hydroxybenzenesulfonate (3c) forms a hydrated noncentrosymmetric phase with a large macroscopic optical nonlinearity 0.5 times of that of DAST at the non-resonant wavelength of λ = 2109 nm, while both (E)-4-(2-(5-(dimethylamino)thiophen-2-yl)vinyl)-1-methylpyridinium 2-amino-3,5-dimethylbenzenesulfonate (3i) and (E)-4-(2-(5-(dimethylamino)thiophen-2-yl)vinyl)-1-methylpyridinium iodide (3a) crystallize in centrosymmetric structures.

研究领域: 有机化学 · 材料科学 · 非线性光学
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RSC Advances · 2014 ·Vol. 4 ·期 87 ·46955-46961 · IF 3.708

A quinoline-functionalized amphiphilic fluorogenic probe for specific detection of trivalent cations

Shengyang Tao,Ying Wei,Chan Wang,Zhaoqi Wang,Pan Fan,Da Shi,Baojun Ding,Jieshan Qiu

A novel fluorescent probe, which has an amphiphilic structure and can selectively detect and distinguish trivalent metal cations, was synthesized. The probe has a hydrophobic quinoline head and a hydrophilic pyridinium tail. This amphiphilic molecular structure makes the molecule exhibit ideal solubility and sensitivity in three kinds of solvents, including EtOH, CH3CN and H2O. The ideal cross-reactivity of this probe in different solvents provided it with the ability to distinguish Fe3+, Cr3+, Al3+, Ru3+ and Au3+ through the PCA method. The detection limits of the probe for trivalent metal cations reach the micromolar range.

研究领域: 分析化学 · 材料科学
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Polymers · 2022 ·Vol. 15 ·期 1 ·14 · IF 4.967

Cationic Chitooligosaccharide Derivatives Bearing Pyridinium and Trialkyl Ammonium: Preparation, Characterization and Antimicrobial Activities

Conghao Lin,Zhanyong Guo,Aili Jiang,Xiaorui Liang,Wenqiang Tan

In this study, chitooligosaccharide-niacin acid conjugate was designed and synthesized through the reaction of chitooligosaccharide and nicotinic acid with the aid ofN,N′-carbonyldiimidazole. Its cationic derivatives were prepared by the further nucleophilic substitution reaction between the chitooligosaccharide-niacin acid conjugate and bromopropyl trialkyl ammonium bromide with different alkyl chain lengths. The specific structural characterization of all derivatives was identified using Fourier Transform Infrared Spectroscopy (FTIR) and Nuclear Magnetic Resonance (NMR), and the degree of substitution was obtained using the integral area ratio of the hydrogen signals. Specifically, the antibacterial activities againstEscherichia coli,Staphylococcus aureus,Pseudoalteromonas citreaandVibrio harveyiwere evaluated using broth dilution methods. In addition, their antifungal activities, includingBotrytis cinerea,Glomerella cingulateandFusarium oxysporum f.sp.cubensewere assayed in vitro using the mycelium growth rate method. Experimental data proved that the samples showed antibacterial activity against four pathogenic bacteria (MIC = 1–0.125 mg/mL, MBC = 8–0.5 mg/mL) and enhanced antifungal activity (50.30–68.48% at 1.0 mg/mL) againstBotrytis cinerea. In particular, of all chitooligosaccharide derivatives, the chitooligosaccharide derivative containing pyridinium and tri-n-butylamine showed the strongest antibacterial capacity against all of the test pathogenic bacteria; the MIC againstVibrio harveyiwas 0.125 mg/mL and the MBC was 1 mg/mL. The experimental results above showed that the introduction of pyridinium salt and quaternary ammonium salt bearing trialkyl enhanced the antimicrobial activity. In addition, the cytotoxicity against L929 cells of the chitooligosaccharide derivatives was evaluated, and the compounds exhibited slight cytotoxicity. Specifically, the cell viability was greater than 91.80% at all test concentrations. The results suggested that the cationic chitooligosaccharide derivatives bearing pyridinium and trialkyl ammonium possessed better antimicrobial activity than pure chitooligosaccharide, indicating their potential as antimicrobial agents in food, medicine, cosmetics and other fields.Keywords:chitooligosaccharide;nicotinylation;pyridinium cation;antibacterial;antifungal

CAS / MDL: 102-69-2
研究领域: 生物化学 · 微生物学 · 药理学
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Surfaces and Interfaces · 2025 · IF 6.3

Enhanced antimicrobial performance of D-A covalent organic framework with pyridinium and quaternary ammonium groups and ROS activity

Baiwei Ma,Xuanyu Lin,Tiaotiao Zhu,Xiaofei Zheng,Juanfang Zhu

s Bacterial infections pose a threat to human health worldwide. Developing antibiotic-free strategies or integrating multiple bactericidal methods is urgently needed for efficient sterilization. Covalent organic frameworks (COFs) have attracted considerable attentions for killing bacteria using photodynamic and photothermal therapy methods, which prevent drug resistance. In this study, a donor–acceptor (D–A)-type COF anchored with pyridinium and quaternary ammonium, named BPDS-COF, was developed to achieve ternary synergistic antibacterial effects. The pyridinium cations generated in situ not only sterilize but also attract and accommodate electrons to thus promote the photoelectric generation of ROS. Additionally, the quaternary ammonium salts provide good antibacterial activity. The simultaneous presence of pyridinium and quaternary ammonium can enhance the hydrophilicity and bacterial adsorption and improve adsorption for oxygen to more easily generate ROS, which are beneficial to sterilization. Moreover, BPDS-COF has the potential to be used as an oral antibacterial dental filler and implant coating material. This ternary synergistic antibacterial strategy could inspire the design of other multifunctional antimicrobial COFs.

研究领域: 材料科学 · 微生物学 · 医学
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RSC Advances · 2015 ·Vol. 5 ·期 51 ·40772-40778 · IF 3.84

Preparation and thermoresponsive properties of helical polypeptides bearing pyridinium salts

Yan Wu,Xi Wang,Ying Ling,Haoyu Tang

Water-soluble polypeptides bearing various pyridinium groups (i.e., pyridinium, 2-methylpyridinium, 3-methylpyridinium, 4-methylpyridinium) and Cl− counter-anions have been prepared by nuleophilic substitutions between poly(γ-3-chloropropyl-L-glutamate) (PCPLG) or poly(γ-6-chlorohexyl-L-glutamate) (PCHLG) and pyridine or y-methyl pyridine (y = 2, 3, and 4). Polypeptides bearing pyridinium groups and BF4− counter-anions were prepared by ion-exchange reactions from the polypeptide–pyridinium conjugates with Cl− counter-anions. CD analysis revealed that water-soluble polypeptides adopted α-helical conformation in solutions with a fractional helicity in the range of 24.7–41.4%. Variable-temperature UV-vis spectroscopy revealed that polypeptides bearing 3-methylpyridinium and BF4− counter-anions (i.e., P11 and P15) showed upper critical solution temperature (UCST)-type transitions in aqueous solutions. The UCST-type phase transition temperatures increased as increasing the hydrophobicity of the spacer groups, the polymer concentrations, and the concentrations of NaBF4.

CAS / MDL: 31137-74-3 132286-79-4
研究领域: 生物化学 · 高分子化学 · 材料科学
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Journal of Saudi Chemical Society · 2017 · IF 2.887

Antimicrobial activities of pyridinium-tailored pyrazoles bearing 1,3,4-oxadiazole scaffolds

Lei Zhou,Pei-Yi Wang,Jian Zhou,Wu-Bin Shao,He-Shu Fang,Zhi-Bing Wu,Song Yang

Herein, a series of pyridinium-tailored 5-trifluoromethylpyrazoles containing 1,3,4-oxadiazole moieties were constructed through coupling key pharmaceutical fragments of pyridinium, pyrazole, and 1,3,4-oxadiazole scaffolds in single molecular architecture. Antimicrobial results suggested that this kind of compounds exhibited significant activities against three types of pathogenic bacteria and six fungal strains in vitro . The minimal EC 50 values of designed compounds against Xanthomonas oryzae pv . oryzae , Ralstonia solanacearum , and Xanthomonas axonopodis pv . citri could reach to 0.467, 1.04, and 0.600   μg/mL, respectively, through tuning and optimizing N -substituents, bridging atom, and alkyl length of the tailor. Antifungal assays revealed that all title molecules possessed considerable activity against Botrytis cinerea with the minimal EC 50 value up to 2.71   μg/mL; and compounds I-8 , I-10 , I-12 , II-12 , and IV-12 showed the strongest growth suppression toward Rhizoctonia solani with EC 50 values ranging from 10.2 to 24.0   μg/mL. Given the above results, this kind of compounds could serve as new lead compounds in the research of antimicrobial chemotherapy.

研究领域: 药理学 · 微生物学 · 有机化学
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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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NEW JOURNAL OF CHEMISTRY · 2020 ·Vol. 44 ·期 9 ·3654-3663 · IF 3.288

Photophysical and electrochemical properties of newly synthesized thioxathone–viologen binary derivatives and their photo-/electrochromic displays in ionic liquids and polymer gels

Dong-Mei Ma,Jing Wang,Hao Guo,Dong-Jin Qian

Thioxanthones (TXs) and viologens (VIOs) are important photo-sensitizers and electron mediators with interesting opto-electrochemical properties and potential applications for novel opto-electrical devices, displays, switches and sensors. Here, we reported the photophysical and electrochemical properties of newly synthesized TX–VIO binary derivatives, and their photo-/electrochromic displays in the ionic liquids and polymer gels. The precursor of TXBr (without the VIO substituent) gave off a blue light emission centered at about 437 nm with a quantum efficiency (QE) of approximately 0.2. For TX-VIOs, their QE was below 0.01; this significant luminescent quenching was attributed to an intramolecular energy transfer from the excited singlet state of TX to electroactive VIO. Thus, these TX–VIOs displayed good photochromic behaviors under ultraviolet and/or visible light radiation. Cyclic voltammograms of TX–VIOs showed two couples of chemically reversible waves centered at approximately −0.43 and −0.90 V (vs. Hg/Hg2Cl2). The former one was attributed to the electron transfer process of TX–VIO2+ ↔ TX–VIO+˙, and the latter one to that of TX–VIO+˙ ↔ TX–VIO0 together with that of TX(red)–VIO2+ ↔ TX(ox)–VIO2+. Finally, sandwiched types of transparent and flexible photo- and electrochromic devices were constructed with the use of TX–VIOs in the ionic liquids and polymeric gels as the light-sensitizer and color display layer. These devices displayed a good transmittance and good reversible color (pink, blue and colorless) change behavior under visible light radiation or an applied bias of −2.4 V.

研究领域: 化学 · 材料科学 · 光电子学
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ANALYST · 2014 ·Vol. 140 ·期 2 ·407-413 · IF 3.906

Novel pyridinium-based tags: synthesis and characterization for highly efficient analysis of thiol-containing peptides by mass spectrometry

Xiaoqiang Qiao,Yanjun Yang,Shijia Liu,Shiheng Chen,Xin Wang,Guangyue Li,Hongyuan Yan,Xun Yang

In this study, a novel type of pyridinium-based tags, 1-[3-[(2-iodo-1-oxoethyl)amino]propyl]-4-methylpyridinium bromide (IMP) and 1-[3-[(2-iodo-1-oxoethyl)amino]propyl]-4-propylpyridinium bromide (IPP), were designed, synthesized, and applied to the derivatization of thiol-containing peptides. With model peptides as the sample, the labeling efficiency and the stability of the peptide derivatives were investigated. The results indicate that nearly 100% derivatization yield was achieved with the developed tags and the peptide derivatives were stable at room temperature for at least one week. Furthermore, improved ionization efficiency and increased charge states were achieved via both matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MS) and electrospray ionization (ESI) MS, of which IPP exhibited the more obvious improvement of ionization efficiency. Further analysis of tryptic digests of bovine serum albumin (BSA) and α-transferrin, showed that increased identification efficiency of the thiol-containing peptides was achieved by combination with IMP or IPP derivatization. For example, the identification efficiency of the thiol-containing peptides of α-transferrin increased more than 42% upon combination with the IMP or IPP derivatives. We anticipate the novel tags are promising for highly efficient thiol-containing peptide identification in proteome research, especially for low concentrations.

研究领域: 生物化学 · 蛋白质组学 · 分析化学
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CHEMICAL ENGINEERING JOURNAL · 2024 · IF 13.3

Bifunctional pyridinium-based Brønsted acidic porous ionic liquid for deep oxidative desulfurization

Jie Yin,Wendi Fu,Jinrui Zhang,Xinmiao Zhang,Wenxiang Qiu,Wei Jiang,Linhua Zhu,Hongping Li,Huaming Li

Porous ionic liquids have been highlighted with special interest for their desirable catalytic activity and extraction properties. Herein, bifunctional porous ionic liquids (denoted UiO-66-BAPILs) were synthesized by dispersing UiO-66 into a pyridinium-based Brønsted acidic ionic liquid ([BSPy][CF 3 SO 3 ]) for oxidative desulfurization. The permanent cavity of UiO-66 moiety in UiO-66-BAPILs was validated as well-preserved by the SO 2 uptake experiments and molecular size simulations. Under the optimum reaction conditions, the sulfur removal could reach up to 99.5% with hydrogen peroxide as the oxidant. Additionally, bifunctional UiO-66-BAPILs were deemed as both extractants and catalysts during the reaction. A possible mechanism has been proposed that UiO-66-BAPILs extract the aromatic sulfur compounds via π···π interactions and C-H···π interactions and meanwhile oxidize them with peroxysulfonic acids and •OH radicals. These findings will open up new avenues to facilitate the catalytic oxidation performance by constructing bifunctional Brønsted acidic porous ionic liquids.

研究领域: 催化化学 · 材料科学 · 环境化学
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Canadian Journal of Chemistry · 2025 · IF 1

The synthesis of novel salicylaldehyde imine derivatives containing pyridinium and selective detection for fluoride and cyanide in organic-aqueous media

Xiangdong Ji,Pengji Yan,Wenqin Yang,Yujiao Peng,Cheng Cao

Two new colorimetric receptors 1 and 2 nitrophenyl as signaling units and imine moieties as binding sites were synthesized via a simple condensation reaction and characterized by 1H NMR, 13C NMR, FTIR, and HRMS. The colorimetric sensing properties of the receptors toward various anions were studied using naked eye detection, UV-vis spectroscopy, and 1H NMR titration. The results show that receptors 1 and 2 exhibit good UV-Vis recognition capabilities for F−, Ac−, and CN−, and can recognize CN− with the naked-eye in a H2O/DMSO (3:7, V/V) solution. The detection limit for CN− recognition by receptors 1 and 2 was as low as 1.31 µmol, and we prepared test papers for detecting anions using these receptors. The Job's plot analysis demonstrates a 1:1 stoichiometric binding ratio between F− and the receptors. The recognition mechanism of CN− was inferred using UV-vis and 1H NMR titrations, HRMS, and theoretical calculations. Such stripes can serve as a practicable colorimetric probe for the detection of ions in many fields and avoid more expensive equipment.

CAS / MDL: 119-26-6
研究领域: 有机化学 · 分析化学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2022 · IF 4.326

Hydrolyzable Quaternary Pyridinium Surfactants: Antimicrobial Profragrances for Controllable Perfume Release

Xinyu Zhou,Ming Liu,Jianwei Han,Limin Wang,Zuobing Xiao,Wei-Hong Zhu

Long-lasting aroma release from the target surfaces is a considerable challenge in the field of fragrances. Here, we report a class of profragrances on the basis of quaternary pyridinium salts (QPS), in which the perfume alcohols are linked with an ester group. Releasing fragrances by hydrolysis of ester bonds in an aqueous environment is aiming at circumventing the bottleneck of long-lasting aroma. Specifically, antimicrobial surfactants and controllable fragrance delivery systems are merged with their intrinsic structural properties. The surface tension of QPS is measured with the critical micelle concentration (CMC) ranging from 0.0029–0.492 mmol L–1 and γ-CMC values of 19.5–34.9 mN m–1. The antibacterial performance of QPS is expressed by the minimum inhibitory concentration (MIC) values, along with an excellent activity on Gram-positive bacteria. Their release performance is determined by the combination of headspace solid-phase microextraction and gas chromatography (HS-SPME–GC) indicative of a significant retention capacity for volatile alcohols. These QPS-based profragrances could be used as a suitable fragrance delivery system in household products.

研究领域: 化学 · 材料科学 · 日用化工
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