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RSC Advances · 2021 ·Vol. 11 ·期 38 ·23802-23814 · IF 3.361

Solubility, thermal and photoluminescence properties of triphenyl imidazole-containing polyimides

Wu Bai,Zhizhi Hu,Yunhua Lu,Guoyong Xiao,Hongbin Zhao,Jianmin Zhu,Zhaobin Liu

In this paper, three kinds of triphenyl imidazole-containing diamines including 2-phenyl-4,5-bis(4-(4-amino-2-trifluoromethylphenoxy)phenyl)imidazole (PBAI), 2-(4-methylphenyl)-4,5-bis(4-(4-amino-2-trifluoromethyl phenoxy)phenyl)imidazole (MPBAI) and 2-(4-trifluoromethylphenyl)-4,5-bis(4-(4-amino-2-trifluoromethylphenoxy)phenyl)imidazole (TFPBAI) were synthesized. Then, a series of polyimide (PI) films were prepared by the solution polymerization of the three diamines and various dianhydrides, such as 4,4′-(hexafluoroisopropylidene)diphthalic anhydride (6FDA), 1,2,4,5-pyromellitic dianhydride (PMDA) and 1,2,3,4-cyclobutanetetracarboxylic dianhydride (CBDA), followed by thermal imidization. The effects of chemical structures on the solubilities and thermal, optical and electrochemical properties of polyimides were explored. All the polyimides exhibited higher glass transition temperatures around 300 °C and excellent solubilities in common polar solvents. The polyimide films derived from CBDA or 6FDA showed better optical properties with light color and transparent characteristics. The fluorescence test showed that the photoluminescence color of CBDA-based polyimide films is in the blue range in the CIE 1931 spectrum, while the polyimide film based on PMDA and 6FDA presented black or weak yellow light. However, all these polyimides in solution exhibited similar blue luminescence. Electrochemical tests indicated that the HOMO and LUMO values of these films were around −6.5 and −3.6 eV, and the energy gap difference was about 3.0 eV. Therefore, the triphenyl imidazole-containing polyimides exhibit comprehensive performance, which will be expected as a new kind of functional material for certain application in the optical and optoelectronics fields.

研究领域: 材料科学 · 光学 · 电化学
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JOURNAL OF HAZARDOUS MATERIALS · 2017 · IF 6.065

A novel “turn-on” fluorescent probe based on triphenylimidazole-hemicyanine dyad for colorimetric detection of CN− in 100% aqueous solution

Shuzhi Liu,Min Yang,Yijiang Liu,Hongbiao Chen,Huaming Li

A new colorimetric fluorescent probe (MCy) for CN − is designed and synthesized based on triphenylimidazole-hemicyanine dyad. The probe shows high selectivity towards CN − in 100% aqueous solution even in the presence of other competitive anions such as F − , Cl − , AcO − , NO 2 − , H 2 PO 4 − , I − , SCN − , SO 4 2− , NO 3 − , HCO 3 − , Br − and S 2− . Upon nucleophilic addition of CN − to the indolium group, the probe displays large blue-shift in UV–vis spectrum and remarkable “turn-on” fluorescence owing to the disruption of intramolecular charge transfer. Meanwhile, the probe also undergoes a naked-eye discernible color change from orange to light pink in the sunlight as well as an obvious fluorescence color change from non-emissive to bright blue under a UV lamp. The detection limit of CN − in aqueous solution can be as low as 20.6   nM, which is much lower than the permissible level of CN − in drinking water according to the WHO. In addition, the probe has been successfully used to determine CN − in real water samples as well as to fabricate test paper kit for CN − detection.

研究领域: 分析化学 · 环境科学
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MICROCHEMICAL JOURNAL · 2023 · IF 4.8

Green-to-blue fluorescence sensor on pesticide starane based on bis-tetraphenylimidazole

Hanqing Wu,Hua Yan,Xiangfei Xu,Hongyu Guo,Fafu Yang

The widespread use of pesticide starane calls for the simple, rapid and on-site detection to mitigate its negative impacts on human health and the environment. In this work, a diamino naphthalene Schiff-base bridging bis-tetraphenylimidazole ( Bis-TPI , red powder, λ abs  = 360 nm) prepared by Schiff-base condensation is developed as an effective fluorescence sensor on pesticide starane with very low detection limitation. Bis-TPI in DMSO-H 2 O with 95% of H 2 O showed weak green fluorescence but strong blue fluorescence when bound to starane. This binding behavior for starane exhibited good sensing selectivity among various ions and pesticides. The detection limitation was as low as 0.015 μM, which is the smallest value of the fluorescence sensor for starane. The 1:1 binding mechanism is clarified as that starane is bound in the opening cavity of Bis-TPI based on hydrogen bond , π-π stacking and hydrophobic action. Bis-TPI in DMSO-H 2 O with 95% of H 2 O is successfully employed to detect starane in various samples including test paper, fresh leaves and real water samples, highlighting its potential as a valuable tool for rapid, simple and on-site examination of starane with high selectivity and sensitivity in agriculture and daily life.

CAS / MDL: 7647-14-5 10026-22-9
研究领域: 分析化学 · 环境科学 · 农业科学
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NEW JOURNAL OF CHEMISTRY · 2023 ·Vol. 47 ·期 10 ·4911-4919 · IF 3.3

A cycloruthenated 2-phenylimidazole: chromogenic sensor for nitrite in acidic buffer and fluoride in CH3CN

Zhen Li,Yirong Wang,Ce Xu,Xianghong Li,Bingguang Zhang

A cyclometalated ruthenium complex (1) using 2-phenylimidazole as the C, N-ligand was successfully synthesized and used as a chromogenic sensor. The as-prepared sensor displayed a good absorption centered at 565 nm in the visible region. Due to strong hydrogen bonding, the complex demonstrated high sensitivity and selectivity to fluoride over other common anions in CH3CN solution. A large red-shift from 565 to 618 nm accompanied by a solution color change from red to green was achieved. However, in CH3CN/Britton-Robinson buffer (V/V = 1 : 9, pH 4.5), the competition with water resulted in no changes for fluoride. Only the presence of nitrite caused the absorption intensity between 400 and 600 nm to decrease remarkably with the solution color fading to yellow. This phenomenon could be attributed to the formation of ruthenium nitrosyl, which was then isolated and characterized by MS, FT-IR and NMR spectra. Therefore, complex 1 can be used as a chromogenic chemosensor to detect fluoride in CH3CN and nitrite in an acidic aqueous system, respectively.

研究领域: 分析化学 · 配位化学
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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2022 · IF 5.141

Dual-response fluorescence sensor for detecting Cu2+ and Pd2+ based on bis-tetraphenylimidazole Schiff-base

Hanqing Wu,Liangbin Lin,Lingyi Zheng,Hongyu Guo,Fafu Yang

Although the fluorescence sensors for Cu 2+ or Pd 2+ had been prepared, the sensor of in-situ detecting both Cu 2+ ion and Pd 2+ ion in aqueous media was rarely concerned. Herein, a bis-tetraphenylimidazole Schiff-base ( Bis-TPI ) with aggregation-induced emission was designed and prepared in yield of 88%. Bis-TPI displayed strong red fluorescence at 550–650 nm in aqueous media and selectively response on detecting Cu 2+ and Pd 2+ with quenched fluorescence. The detection limits attained 8.3 × 10 -7 M for Cu 2+ and 9.2 × 10 -7 M for Pd 2+ , respectively. The mutual interference on detecting Cu 2+ and Pd 2+ in their coexistence system was eliminated by the masking reagent of adenosine triphosphate for Cu 2+ , realizing the detection of Cu 2+ and Pd 2+ sequentially. The sensing mechanism of 1:1 binding system was supported by FT-IR spectra, binding MS spectra, 1 H NMR spectra and fluorescence Job’s plot. Moreover, Bis-TPI showed good fluorescence bioimaging property and achieved in-situ detection on Cu 2+ and Pd 2+ in living-cell system, implying the application prospect on in-situ sensing Cu 2+ and Pd 2+ in both vitro environment and vivo assay.

研究领域: 分析化学 · 生物成像 · 环境科学
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Journal of Environmental Chemical Engineering · 2025 · IF 7.2

Selective flotation separation of chalcopyrite from pyrite using 2-phenylimidazoline as a collector: Flotation performance and surface adsorption mechanism

Songlin Chen,Zhihao Shen,Zhengyong Song,Guang Han,Qicheng Feng

The flotation separation of Cu–Fe sulfide minerals often encounters challenges due to the use of inhibitors, which can lead to difficulties in recovering precious metals and the activation of inhibited minerals, thereby limiting the overall efficiency of resource utilization. Therefore, the exploration of highly selective collectors is of great significance. In this study, 2-phenylimidazoline (2-PI) was investigated as a novel collector for the selective flotation separation of chalcopyrite from pyrite. The variations in the surface properties of minerals were analyzed by means of contact angle tests, zeta potential tests, X-ray photoelectron spectroscopy (XPS), Fourier Transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), and localized electrochemical impedance spectroscopy (LEIS) tests. Flotation experiments indicated that after being treated with 1 × 10 –5 mol/L 2-PI, the flotation recovery of chalcopyrite exceeded 90 %, while that of pyrite was below 10 %. The results of contact angle, zeta potential, AFM, and LEIS tests demonstrated that 2-PI exhibited a stronger affinity for the surface of chalcopyrite. XPS and FT-IR analyses revealed that 2-PI underwent chemical adsorption on the chalcopyrite surface, with no significant adsorption on the pyrite surface. Consequently, 2-PI has the potential to be an alternative collector for the flotation separation of Cu–Fe sulfide minerals and shows promising applications for achieving the selective separation of chalcopyrite and pyrite in the absence of inhibitors.

研究领域: 矿物加工工程 · 化学工程 · 材料科学
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JOURNAL OF ELASTOMERS AND PLASTICS · 2013 · IF 0.623

A novel single component epoxy resin adhesive with microcapsule latent curing agent of 2-phenylimidazole/polymethyl acrylic glycidyl ester

Aijie Ma,Qiuyu Zhang,Hepeng Zhang,Youqiang Shi,Yu Liu

2-Phenylimidazole (2-PZ) and polymethyl acrylic glycidyl ester (PGMA) are performed to fabricate a novel microcapsule latent curing agent of 2-PZ/PGMA by solvent evaporation method with 2-PZ as the core material and PGMA as the shell material. A novel single-component 2-PZ/PGMA/epoxy adhesive is also prepared by mixing 2-PZ/PGMA with epoxy resin matrix. The 2-PZ/PGMA microcapsules are characterized using scanning electron microscopy and granulometer. The curing kinetics and thermal properties of 2-PZ/PGMA/epoxy resin system are also investigated using differential scanning calorimeter, Fourier transform infrared spectrometer, and thermogravimetric analysis. Results show that 2-PZ/PGMA has good sphericity and narrow diameter distribution. The curing process of the 2-PZ/PGMA/epoxy resin system contains autocatalytic mechanism. Compared with that of pure epoxy, the presence of the 2-PZ/PGMA has little effect on thermal stability for the epoxy.

研究领域: 材料科学 · 化学工程
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EUROPEAN POLYMER JOURNAL · 2019 · IF 3.621

Benzoxazine monomers containing triphenylimidazole: Polymerization of monomers and properties of polybenzoxazines

Xufeng Li,Yijiang Liu,Hongbiao Chen,Huaming Li

In this study, two novel benzoxazine monomers containing triphenylimidazole (TBZ) and triphenylimidazolium (MTBZ) moieties are synthesized and fully characterized. The thermal ring-opening polymerization process of the two monomers is monitored by the 1 H NMR and GPC analyses, which demonstrates that such a polymerization proceeds through a rearrangement of ketal-type linkage in the main chain into Mannich-type polymer along with the fast increasing in molecular weight. The structures of the triphenylimidazole-containing polybenzoxazines, poly-TBZ and poly-MTBZ, are verified by 1 H NMR and FT-IR spectroscopies, and the thermal and mechanical properties of such polybenzoxazines are investigated by TGA and DMA analyses. Owing to the good solubility of poly-TBZ and poly-MTBZ in common organic solvents, poly-TBZ can be easily converted into poly-MTBZ through a facile post-modification approach. More importantly, the poly-TBZ shows the acid-dependent spectral properties due to formation of amine salts, whereas poly-MTBZ can be used as a chemodosimeter for the detection of Ag + , which exhibits high selectivity, good linearity and naked-eye distinguishable color change. This strategy can be utilized to prepare triphenylimidazole-containing polybenzoxazines with good solubility and tunable spectral properties, thereby extending their functionalities and applications.

CAS / MDL: 90-02-8 74-88-4
研究领域: 材料科学 · 高分子化学
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CORROSION SCIENCE · 2023 · IF 8.3

Synergistic inhibition of azoles compounds on chloride-induced atmospheric corrosion of copper: Experimental and theoretical characterization

Xiao-Ze Ma,Guang-Yi Cai,Xiang-Kang Cao,Xin-Xin Zhang,Ling-Dong Meng,Ze-Hua Dong

Synergistic implementation of corrosion inhibitors is an efficient and economic method for metal protection. The adsorption dynamics and inhibition behavior of 2-phenyl imidazoline (2-PI) and benzotriazole (BTA) are investigated in atmospheric and aqueous environments by electrochemical and quartz crystal microbalance sensors. Moreover, their synergistic mechanisms are illustrated from molecule scales by theoretical calculations. Electrochemical tests show that 2-PI and BTA exhibit promising synergistic effects on the corrosion of copper with inhibition efficiency up to 99.1% in 0.1 mol/L NaCl solution and 94.1% in the atmosphere, respectively. In addition, the adsorption kinetics of inhibitors on copper obey a pseudo-first-order kinetic model characteristic of exponential damping. Quantum chemical and molecule dynamic calculations also suggest that there exists an intermolecular interaction between 2-PI and BTA molecules in a parallel adsorption manner when they are co-adsorbed on the surface of copper.

CAS / MDL: 95-14-7 936-49-2
研究领域: 材料科学 · 电化学 · 理论计算
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MATERIALS CHEMISTRY AND PHYSICS · 2021 · IF 4.094

Investigation on initial atmospheric corrosion of copper and inhibition performance of 2-phenyl imidazoline based on electrical resistance sensors

Shan Wan,ZeHua Dong,Xinpeng Guo

The initial atmospheric corrosion of copper was investigated by electrical resistance sensor under different environmental factors (relative humidity, temperature, and NaCl loading density). The corrosion rate of Cu increases evidently with NaCl loading density, temperature and RH, but decreases with prolonged test. 2-phenyl imidazoline (2-PI) presents increasing inhibition efficiency on Cu with elevated temperatures at low NaCl loading density (≤40 μg/cm 2 ), mainly due to that elevated temperature enhances the vapour pressure of 2-PI, however, 2-PI shows inferior performance on pre-corroded Cu at high NaCl loading density, possibly due to that the defective corrosion product layer formed at high RH retards the adsorption of 2-PI. Finally, molecular dynamic simulations were conducted to evidence the competitive adsorption advantage of 2-PI against H 2 O on Cu 2 O surface through chelation of 1-N of imidazoline with Cu(I).

CAS / MDL: 936-49-2
研究领域: 材料科学 · 腐蚀与防护 · 化学工程
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CORROSION SCIENCE · 2020 · IF 6.479

Inhibition of 2-phenyl imidazoline on chloride-induced initial atmospheric corrosion of copper by quartz crystal microbalance and electrochemical impedance

Shan Wan,Xiao-Ze Ma,Chun-Hui Miao,Xin-Xin Zhang,Ze-Hua Dong

Initial atmospheric corrosion of clean copper and NaCl-deposited copper was investigated by quartz crystal microbalance and electrochemical impedance spectroscopy. 2-phenyl imidazoline (2-PI) exhibits increasing inhibition efficiency with temperature on chloride-induced atmospheric corrosion of Cu. However, on the NaCl-deposited Cu, adsorption amount of 2-PI is much higher than that on clean Cu possibly due to that rough corrosion products entrap lots of 2-PI molecules. The adsorption of 2-PI on corroded Cu is suggested to obey a capillary condensation and entrapment mechanism, but in dry argon atmosphere, it obeys a simple pseudo first-order model for lack of corrosion products.

研究领域: 材料科学 · 腐蚀与防护 · 电化学
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Foods · 2025 ·Vol. 14 ·期 8 ·1292 · IF 5.1

Development and Application of a Rapid Detection Technique for 2-Amino-1-methyl-6-phenyl-imidazo [4,5-b] Pyridine in Meat Products Based on Hydrogel-Molecular-Imprinting Electrochemical Sensing Technology

Chunxiao Li,Xiaolei Zhao,Xiaofei Yin,Shuting Zhang,Jinxing He

2-amino-1-methyl-6-phenyl-imidazo [4,5-b] pyridine (PhIP) is a harmful compound that is formed during the high-temperature processing of meat products, and the risk of cancer may be increased with the prolonged intake of foods containing high levels of PhIP. This study aimed to develop an innovative detection method specifically for PhIP in meat products. Utilizing hydrogel-molecular-imprinting electrochemical sensing technology, the preparation conditions of molecularly imprinted hydrogels (MIHs) were optimized. Consequently, a highly selective and rapid detection method for PhIP was successfully established, integrated with an electrochemical workstation. The results indicate that the prepared MIHs exhibit an excellent specific recognition performance for PhIP. The sensor exhibited a linear response within the concentration range of 1.0–200.0 ng/mL, with a detection limit of 0.07 ng/mL (S/N = 3) under optimized conditions. In addition, the accuracy and reliability of the method were verified by spiked recovery experiments, and the recoveries ranged from 75.9% to 108.8%, which demonstrated its high accuracy and potential for practical application.

研究领域: 食品安全 · 分析化学 · 生物医学工程
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