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CATALYSIS LETTERS · 2020 ·Vol. 151 ·期 3 ·901-908 · IF 2.482

Accurate Understanding the Catalytic Role of MnO2 in the Oxidative-Coupling of 2-naphthols into 1,1′-bi-2-naphthols

Wu Yuting,Yang Long,Wu Bo,Li Jie,Liu Binyao,Ke Gaili,Dong Faqin,Zhou Yong,He Huichao

It has been reported that β -MnO 2 has photocatalytic activity for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols. Nevertheless, it is hard to exclude the possibility that the oxidative-coupling of 2-naphthols is initiated by β -MnO 2 catalysis in dark due to the insufficient investigations in the related reports. In the present work, the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols with different phases MnO 2 catalysis in dark and under visible-light irradiation were systematically investigated. The results revealed that the oxidative-coupling of 2-naphthols is jointly initiated by MnO 2 catalysis and O 2 -oxidation, not by MnO 2 photocatalysis. Among the α -MnO 2 , β -MnO 2 , γ -MnO 2 and δ -MnO 2 catalysis, β -MnO 2 catalysis has the optimal performance, its selectivity for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols is close to 100%, and its catalytic capacity could be well retained after multiple using. Our findings provide comprehensive and accurate understanding the catalytic role of MnO 2 for the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols. Graphic In the present work, the oxidative-coupling of 2-naphthols into 1,1′-bi-2-naphthols was proved to be jointly initiated by MnO 2 catalysis and O 2 -oxidation, not by MnO 2 photocatalysis. β -MnO 2 has the optimal catalytic activity for the oxidative-coupling of 2-naphthols relative to α -MnO 2 , γ -MnO 2 and δ -MnO 2 .

研究领域: 催化化学 · 有机合成 · 材料化学 · 物理化学 · 纳米催化
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ELECTROCHIMICA ACTA · 2014 · IF 4.086

A facile one-step in situ synthesis of copper nanostructures/graphene oxide as an efficient electrocatalyst for 2-naphthol sensing application

Junhua Li,Jun Li,Haibo Feng,Yaqian Zhang,Jianbo Jiang,Yonglan Feng,Mansheng Chen,Dong Qian

A copper nanostructures-graphene oxide (Cu/GO) hybrid as a new electrocatalyst for highly sensitive detection of 2-naphthol (2-NAP) was successfully synthesized by a one-pot and in situ chemical reduction approach. The characterization results reveal that the cubic Cu nanostructures are tightly attached onto the GO sheets in the resulting hybrid. A lower oxidation potential and a larger peak current were observed for the 2-NAP oxidation at the Cu/GO modified electrode, demonstrating the synergistic electrocatalysis from Cu nanostructures and GO sheets. Consequently, the Cu/GO hybrid exhibits a low detection limit (5.0   nM) and wide linear ranges (0.1–4.0   μM and 4.0–130.0   μM) when used as a sensing material for the sensitive detection of 2-NAP. Finally, the fabricated sensor was successfully applied in the detection of 2-NAP in real samples and satisfactory recoveries in the range of 99.3%–104.0% were achieved.

CAS / MDL: 7447-39-4 135-19-3
研究领域: 材料科学 · 分析化学 · 环境科学
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Nanomaterials · 2022 ·Vol. 12 ·期 20 ·3636 · IF 5.719

Organo-Vermiculites Modified by Aza-Containing Gemini Surfactants: Efficient Uptake of 2-Naphthol and Bromophenol Blue

Jianchao Gong,Tingting Wang,Wei Zhang,Lin Han,Mingxiao Gao,Tianen Chen,Tao Shen,Yaxiong Ji

To explore the effect of spacer structure on the adsorption capability of organo-vermiculites (organo-Vts), a series of aza-containing gemini surfactants (5N, 7N and 8N) are applied to modify Na-vermiculite (Na-Vt). Large interlayer spacing, strong binding strength and high modifier availability are observed in organo-Vts, which endow them with superiority for the adsorption of 2-naphthol (2-NP) and bromophenol blue (BPB). The maximum adsorption capacities of 5N-Vt, 7N-Vt and 8N-Vt toward 2-NP/BPB are 142.08/364.49, 156.61/372.65 and 146.50/287.90 mg/g, respectively, with the adsorption processes well fit by the PSO model and Freundlich isotherm. The quicker adsorption equilibrium of 2-NP than BPB is due to the easier diffusion of smaller 2-NP molecules into the interlayer space of organo-Vts. Moreover, stable regeneration of 7N-Vt is verified, with feasibility in the binary-component system that is demonstrated. A combination of theoretical simulation and characterization is conducted to reveal the adsorption mechanism; the adsorption processes are mainly through partition processes, electrostatic interaction and functional interactions, in which the spacer structure affects the interlayer environment and adsorptive site distribution, whereas the adsorbate structure plays a role in the diffusion process and secondary intermolecular interactions. The results of this study demonstrate the versatile applicability of aza-based organo-Vts targeted at the removal of phenols and dyes as well as provide theoretical guidance for the structural optimization and mechanistic exploration of organo-Vt adsorbents.Keywords:organo-vermiculite;aza-containing gemini surfactant;2-Naphthol;bromophenol blue;adsorption

研究领域: 环境科学 · 材料科学
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JOURNAL OF INDUSTRIAL AND ENGINEERING CHEMISTRY · 2023 · IF 6.1

1-(2-Pyridylazo)-2-naphthol as a synergistic additive for improving throwing power of through hole copper electronic electroplating

Lei Jin,Zhao-Yun Wang,Zhuan-Yun Cai,Jia-Qiang Yang,An-Ni Zheng,Fang-Zu Yang,De-Yin Wu,Dongping Zhan

In this work, we develop a novel 1-(2-Pyridylazo)-2-naphthol (PAN)-based acidic sulfate copper electronic electroplating process for compact, homogeneous and conformal copper thickening of through hole (TH). The adsorption characteristics, electrochemical properties and the interaction mechanisms of three additives (PEG, SPS and PAN) are studied in detail. Scanning electron microscope (SEM) and optical microscope (OM) reveal that PAN can make the copper coating in fine grains and high throwing power of 90.35% in TH without an overhang phenomenon. Theoretical calculations illustrate that the binding energies between additive molecules and copper surface decrease in the order: PAN > SPS >  PEG . Cyclic voltammetry experiments at rotating rates of 1200 and 200 r/min prove that PAN itself can accelerate and weakly suppress copper electrodeposition at the center and mouth of TH, respectively. PAN behaves respectively the synergistic and antagonistic effects with PEG at the mouth and center of TH, and the weakly synergistic effects with SPS both at the mouth and center of TH. The addition of PAN to the virgin make-up solution (VMS) containing PEG and SPS causes decreasing the relative electric charge (Δ Q ) at high and low rotating rates from 18.52 ± 0.08% to 8.25 ± 0.05%, which satisfies the closer copper electronic electroplating rate at the center and mouth of TH. The effective and complicated synergistic effects of the additives PEG, SPS and PAN can achieve compact, homogeneous and conformal copper thickening of TH.

研究领域: 材料科学 · 电化学工程
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JOURNAL OF ELECTROANALYTICAL CHEMISTRY · 2019 · IF 3.218

Electrochemical mineralization of 1-naphthol and 2-naphthol using boron-doped diamond anodes: Factor analysis and mechanisms study

Wei Chen,Jiayue Dong,Sihan Zhou,Chunyong Zhang,Degang Fu

1-naphthol (1-NAP) and 2-naphthol (2-NAP) are both hazardous pollutants which pose great threat to our living environment. In the current work, a comparative investigation on the electrochemical mineralization of 1-NAP and 2-NAP using boron-doped diamond (BDD) anode was presented. Experiments were carried out using synthetic 1-NAP or 2-NAP solutions containing Na 2 SO 4 as supporting electrolyte . A two-level factorial design methodology was adopted to optimize the mineralization process, six mathematical models were thus constructed and used to explore the structure-property relation involved. The results obtained suggested that 1-NAP was easier and faster to break down than 2-NPA under the same oxidation conditions, which were in line with the outcome obtained from cyclic voltammetry , HPLC and TOC measurements. To understand the destruction mechanism, the electron structures of 1-NAP and 2-NAP were further examined by the quantum chemistry calculations with density functional theory. It was also found that the results from frontier orbital analysis could well explain the differing mineralization performances recorded in BDD anode cell. Finally, with the aid of LC/MS analysis, the oxidation pathways of 1-NAP or 2-NAP on BDD anodes were proposed.

研究领域: 环境科学 · 电化学
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Journal of Environmental Sciences · 2010 · IF 1.412

Biodegradation of 2-naphthol and its metabolites by coupling Aspergillus niger with Bacillus subtilis

Shuyan Zang,Bin Lian,Juan Wang,Yanjie Yang

To explore biodegradation of 2-naphthol and its metabolites accumulated in wastewater treatment, a series of bio-degradation experiments were conducted. Two main metabolites of 2-naphthol, 1,2-naphthalene-diol and 1,2-naphthoquinone, were identified by high-performance liquid chromatography with standards. Combining fungus Aspergillus niger with bacterium Bacillus subtilis in the treatment enhanced 2-naphthol degradation efficiency, lowered the accumulation of the two toxic metabolites. There were two main phases during the degradation process by the kinetic analysis: 2-naphthol was first partly degraded by the fungus, producing labile and easily accumulated metabolites, and then the metabolites were mainly degraded by the bacterium, attested by the degradation processes of 1,2-naphthalene-diol and 1,2-naphthoquinone as sole source of carbon and energy. Sodium succinate, as a co-metabolic substrate, was the most suitable compound for the continuous degradation. The optimum concentration of 2-naphthol was 50 mg/L. The overall 2-naphthol degradation rate was 92%, and the COD Cr removal rate was 80% on day 10. These results indicated that high degradation rate of 2-naphthol should not be considered as the sole desirable criterion for the bioremediation of 2-naphthol-contaminated soils/wastewater.

CAS / MDL: 132-86-5 524-42-5
研究领域: 环境科学 · 微生物学
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MICROCHIMICA ACTA · 2011 ·Vol. 175 ·期 3 ·341-346 · IF 2.578

Determination of phenolic compounds in water samples by HPLC following ionic liquid dispersive liquid-liquid microextraction and cold-induced aggregation

Jiang Xinyu,Zhang Hui,Chen Xiaoqing

We report on the determination of bisphenol A and 2-naphthol in water samples using ionic liquid cold-induced aggregation dispersive liquid-liquid microextraction combined with HPLC. Parameters governing the extraction efficiency (disperser solvent, volume of extraction and disperser solvent, pH, temperature, extraction time) were optimized and resulted in enrichment factors of 112 for bisphenol A and of 186 for 2-naphthol. The calibration curve was linear with correlation coefficients of 0.9995 and 0.9998, respectively, in the concentration range from 1.5 to 200 ng mL −1 . The relative standard deviations are 2.3% and 4.1% (for n  = 5), the limits of detection are 0.58 and 0.86 ng mL −1 , and relative recoveries in tap, lake and river water samples range between 100.1 and 108.1%, 99.4 and 106.2%, and 97.1 and 103.8%, respectively. IL-CIA-DLLME has a high enrichment factor (112, 186), acceptable relative recovery (97.1%–108.1%), good repeatability (2.3%, 4.1%) and a wide linear range(1.5–200 ng mL −1 ) for the determination of bisphenol A and 2-naphthol.

研究领域: 分析化学 · 环境科学
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SEPARATION SCIENCE AND TECHNOLOGY · 2022 · IF 2.799

Novel multi-hydroxyl containing organo-vermiculite for effective removal of 2-Naphthol: adsorption studies and model calculations

Yaxun Sun,Xin Li,Tingting Wang,Yaxiong Ji,Yihang Yue,Yong Li,Shifeng Wang

In this study, a multi-hydroxyl-containing gemini surfactant 1,4-bis(hexadecyldimethylammonio)-2,3-dihydroxylbutane dibromide (BHHB) is firstly introduced to modify vermiculite (Na-Vt) for 2-naphthol adsorption. Successful functionalization is verified from the enhanced hydrophobicity, increased organic carbon content, enlarged interlayer spacing and decreased surface area of BHHB-Vt over Na-Vt, constructing favorable structural microenvironments for 2-naphthol retention. Effective adsorptivity and excellent reusability are obtained from the comparison of BHHB-Vt (198.16 mg/g) over Na-Vt (43.26 mg/g C0 = 300 mg/L, V = 30 mL, m = 0.03 g, t = 3 h). Partition process, hydrogen bond, OH-π interaction and electrostatic attraction are responsible for the adsorption, where OH-π interaction is stronger than hydrogen bond. The agreement of pseudo-second order and Langmuir models indicate a chemical adsorption feature on homogeneous surface. Notably, hydrogen groups connected at different carbon atoms exhibit less steric hindrance and wider molecule orbitals, providing stronger interactions between the adsorbent and targeted organic pollutant.

CAS / MDL: 1318-00-9
研究领域: 环境科学 · 材料化学
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RSC Advances · 2024 ·Vol. 14 ·期 30 ·21307-21317 · IF 3.9

Highly efficient and stable adsorption of lithium from brine with microcapsules containing 1-phenylazo-2-naphthol and trioctylphosphine oxide

Tian Xie,Han Qu,Chao Zhang,Zheng Li

Lithium extraction from salt lake brine is still challenging due to the existence of similar elements, e.g. sodium. In the present work, polysulfone (PSF) microcapsules containing 1-phenylazo-2-naphthol (HS) and trioctylphosphine oxide (TOPO) as extractants were successfully prepared by microfluidic technology for the separation of Li+ from brine with Li+ and Na+. The morphology, composition, and structure of HS-TOPO-based microcapsules were characterized systematically. The results showed that microcapsules consisting of 20 wt% (m m−1) polysulfone and 80 wt% (m m−1) 1-phenylazo-2-naphthol-trioctylphosphine oxide as the extractant, which was labeled as PSF/HS-TOPO-2/8, exhibited the best performance for Li+ adsorption. The separation factor (SF) of Li+ over Na+ is up to 653 and the adsorption capacity for Li+ in the simulated brine could reach 3.67 mg g−1 for microcapsules PSF/HS-TOPO-2/8, which demonstrated that Li+ can be separated with high selectivity. Besides, the kinetic results demonstrated that the adsorption followed quasi-secondary adsorption kinetic models, indicating that the adsorption mechanism of lithium by microcapsules involved chemisorption. After ten cycles of adsorption–elution, the maximum equilibrium adsorption capacity still remained at 87%. All these results demonstrate that PSF/HS-TOPO-2/8 microcapsules can be used as an efficient adsorber for the adsorption of Li+ from brine with high selectivity and stability.

CAS / MDL: 1310-66-3 25135-51-7
研究领域: 材料科学 · 化学工程
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NEW JOURNAL OF CHEMISTRY · 2018 ·Vol. 42 ·期 6 ·4324-4330 · IF 3.201

A selective colorimetric sensing strategy for cysteine based on an indicator-displacement mechanism

Zhonghua Xue,Lulu Xiong,Hao Peng,Honghong Rao,Xiuhui Liu,Xiaoquan Lu

Rapid determination of cysteine in aqueous solution is important for the diagnosis and treatment of some diseases. We herein present a simple yet facile colorimetric indicator-displacement assay for cysteine in aqueous solution with a sensitive optical readout based on the competitive binding affinity between the 1-(2-pyridylazo)-2-naphthol (PAN) indicator and cysteine target towards the host Zn2+. In the absence of cysteine, Zn2+ can induce an appreciable yellow-to-pink color change for the PAN solution through the formation of a PAN–Zn2+ complex. However, adding cysteine to the above PAN–Zn2+ complex solution resulted in a ligand exchange reaction between PAN and cysteine with about 57 nm blue-shift in the absorbance maximum (from 527 nm to 470 nm), accompanied by a visible color change of the solution from pink to yellow. The obtained indicator-displacement assay provides a good detecting performance for cysteine with a detection limit of 7.32 μM (S/N = 3) using a UV/vis spectrometer as well as with a good linear range from 25 to 1000 μM. In particular, the proposed sensing system could be successfully used for the fabrication of a colorimetric INHIBIT logic gate and converted into the test paper and image capture analytical devices for the onsite visual determination of cysteine in practical applications.

CAS / MDL: 85-85-8
研究领域: 分析化学 · 医学诊断
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BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN · 2021 ·Vol. 95 ·期 1 ·116-120 · IF 5.488

Construction of Supramolecular Fluorescent Probe by a Water-Soluble Pillar[5]arene and Its Recognition of Carbonate Ion

Zhu Xin Yi,Yang Xi Nan,Wu Heng,Tao Zhu,Xiao Xin

The interaction between pyridine pillar[5]arene (PyP5) and 2-naphthol with the former as the host molecule and the latter as the guest molecule is studied by fluorescence spectroscopy and NMR techniques, and the results show that PyP5 forms a 1:1 host-guest inclusion complex with 2-naphthol. Although free 2-naphthol has strong fluorescence, it is quenched in 2-naphthol@PyP5. Experiments were conducted with 2-naphthol@PyP5 as a fluorescent probe to detect different anions with results showing that only CO32− causes a significant enhancement of the fluorescence of the fluorescent probe. Due to this high selectivity and high sensitivity, the fluorescent probe 2-naphthol@PyP5 may open up an effective way for the detection of CO32−.

研究领域: 超分子化学 · 分析化学
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JOURNAL OF CHROMATOGRAPHY A · 2024 · IF 3.8

Preparation and evaluation of a 1,1′-bi-2-naphthol-based chiral macrocycle bonded silica chiral stationary phase for high performance liquid chromatography

Li-Qin Yu,Rui-Xue Liang,Juan Chen,Sheng-Ming Xie,Bang-Jin Wang,Jun-Hui Zhang,Li-Ming Yuan

Macrocycles play vital roles in supramolecular chemistry and chromatography. 1,1′-Bi-2-naphthol (BINOL)-based chiral polyimine macrocycles are an emerging class of chiral macrocycles that can be constructed by one-step aldehyde-amine condensation of BINOL derivatives with other building blocks. These macrocycles exhibit good characteristics, such as facile preparation, rigid cyclic structures, multiple chiral centers, and defined molecular cavities, that make them good candidates as new chiral recognition materials for chromatographic enantioseparations. In this study, a BINOL-based [2+2] chiral polyimine macrocycle was synthesized by one-step condensation of enantiopure ( S )-2,2′-dihydroxy-[1,1′-binaphthalene]-3,3′-dicarboxaldehyde with (1R,2R)-1,2-diaminocyclohexane. The product was modified with 5-bromo-1-pentene and then attached to thiolated silica using click chemistry to construct a new chiral stationary phase (CSP). The enantioselectivity of the new CSP was explored by separating various racemates under normal phase (NP) and reversed phase (RP) high performance liquid chromatography (HPLC). Thirteen racemates and eight racemates were enantioseparated under the two separation modes, respectively, including chiral alcohols, phenols, esters, ketones, amines, and organic acids. Among them, nine racemates achieved baseline separation under NP-HPLC and seven racemates achieved baseline separation under RP-HPLC. High resolution separation was observed with benzoin ( Rs = 5.10), epinephrine ( Rs = 4.98), 3-benzyloxy-1,2-propanediol ( Rs = 4.42), and 4,4′-dimethylbenzoin ( Rs = 4.52) in NP-HPLC, and with 4-methylbenzhydrol ( Rs = 4.72), benzoin ethyl ether ( Rs = 3.79), 1-phenyl-1-pentanol ( R s = 3.68), and 1-(3-bromophenyl)ethanol ( Rs = 3.60) in RP-HPLC. Interestingly, the CSP complemented Chiralcel OD-H, Chiralpak AD-H, and CYCLOBOND I 2000 RSP columns for resolution of these test racemates, separating several racemic compounds that could not be well separated by the three commercially available columns. The influences of injected sample amount on separation were also evaluated. It was found that the column exhibited excellent stability and reproducibility after hundreds of injections, and the relative standard deviations ( n = 5) of the retention time and resolution were less than 0.49% and 0.69%, respectively. This study indicates that the BINOL-based chiral macrocycle has great potential for HPLC enantioseparation.

研究领域: 分析化学 · 色谱技术 · 有机化学
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