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Application of novel metal-organic framework [Zr-UiO-66-PDC-SO₃H]FeCl₄ in the synthesis of dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives.

ABSTRACT: In the current paper, we produce a new metal-organic framework (MOF) based on Zr metal, [Zr-UiO-66-PDC-SO₃H]FeCl₄, via an anion exchange method, which is fully characterized by FT-IR, SEM with elemental mapping and EDX, FE-SEM and TEM. Furthermore, the use of [Zr-UiO-66-PDC-SO₃H]FeCl₄ as a porous catalyst was examined for the one-pot synthesis of novel dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives by reaction of 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione, 2-hydroxynaphthalene-1,4-dione and various aldehydes at 100 °C with good to excellent yields.

SUBMITTER: Jalili F

PROVIDER: S-EPMC8985156 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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Application of novel metal-organic framework [Zr-UiO-66-PDC-SO3H]FeCl4 in the synthesis of dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives.

Jalili Fatemeh F Zarei Mahmoud M Zolfigol Mohammad Ali MA Khazaei Ardeshir A

RSC advances 20220323 15

In the current paper, we produce a new metal-organic framework (MOF) based on Zr metal, [Zr-UiO-66-PDC-SO3H]FeCl4, via an anion exchange method, which is fully characterized by FT-IR, SEM with elemental mapping and EDX, FE-SEM and TEM. Furthermore, the use of [Zr-UiO-66-PDC-SO3H]FeCl4 as a porous catalyst was examined for the one-pot synthesis of novel dihydrobenzo[g]pyrimido[4,5-b]quinoline derivatives by reaction of 6-amino-1,3-d ...[more]

PMID: 35424891

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Synthesis and application of [Zr-UiO-66-PDC-SO3H]Cl MOFs to the preparation of dicyanomethylene pyridines via chemical and electrochemical methods.

Project description:A metal-organic framework (MOF) with sulfonic acid tags as a novel mesoporous catalyst was synthesized. The precursor of Zr-UiO-66-PDC was synthesized both via chemical and electrochemical methods. Then, zirconium-based mesoporous metal-organic framework [Zr-UiO-66-PDC-SO3H]Cl was prepared by reaction of Zr-UiO-66-PDC and SO3HCl. The structure of [Zr-UiO-66-PDC-SO3H]Cl was confirmed by FT-IR, PXRD, FE-SEM, TEM, BET, EDX, and Mapping analysis. This mesoporous [Zr-UiO-66-PDC-SO3H]Cl was successfully applied for the synthesis of dicyanomethylene pyridine derivatives via condensation of various aldehyde, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and malononitrile. At the electrochemical section, a green electrochemical method has successfully employed for rapid synthesis of the zirconium-based mesoporous metal-organic framework UiO-66-PDC at room temperature and atmospheric pressure. The synthesized UiO-66-PDC has a uniform cauliflower-like structure with a 13.5 nm mean pore diameter and 1081.6 m2 g-1 surface area. The described catalyst [Zr-UiO-66-PDC-SO3H]Cl was also employed for the convergent paired electrochemical synthesis of dihydropyridine derivatives as an environmentally friendly technique under constant current at 1.0 mA cm-2 in an undivided cell. The proposed method proceeds with moderate to good yields for the model via a cooperative vinylogous anomeric based oxidation.

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Hydrolysis of Dimethyl Phosphite by Zr- and Hf-UiO-66.

Project description:Metal-organic frameworks have been utilized as heterogeneous catalysts for the degradation of chemical warfare agents, typically organophosphorous nerve agents. Vibrational spectroscopy techniques coupled with nuclear magnetic resonance (NMR) were utilized to study the adsorption and degradation of dimethyl phosphite (DMP), a simulant molecule of the organophosphorus nerve agent Soman (GD), by Zr- and Hf-UiO-66 as a function of particle size, defect type, and defect density. Defective Zr- and Hf-UiO-66 have been synthesized via a modulated synthesis protocol to engineer missing linker and missing cluster defects into the crystal structure. The adsorption of DMP to UiO-66 was observed to be surface-limited, suggesting maximal DMP adsorption occurs with maximized external surface area. In addition, Hf-UiO-66 samples engineered with large quantities of missing cluster defects are observed to more efficiently hydrolyze DMP into phosphonic acid when compared to less-defective samples. The increase in reactivity is attributed to the greater accessibility of the internal particle volume and, thus, access to a higher number of Lewis-acidic open metal sites, facilitated by missing cluster defects. Taken together, these two observations indicate that to create maximally efficient MOF catalysts for chemical warfare agent degradation one must obtain frameworks with large surface area to maximize adsorption of the simulant as well as a large accessible free volume obtained through the introduction of missing cluster defects to maximize the degradation of the simulant at the Lewis acid sites found in the interior of the framework.

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Vibrational spectroscopy investigation of defects in Zr- and Hf-UiO-66.

Project description:Defect engineering in metal-organic framework compounds has allowed for improvements in catalysis-based functionalities, gas sensing, and gas storage. Metal-organic framework UiO-66 compounds with Zr- and Hf-based metal secondary building units were studied with Raman and infrared vibrational spectroscopy. Missing linker and missing cluster defects were engineered into the crystal structure via a modulated synthesis technique. Missing cluster defects in Hf-UiO-66 are first characterized by powder X-ray diffraction (PXRD) whereby two low-angle peaks were fit to extract the relative quantity of reo topology in four defective samples. A monotonic red-shift of the Raman-active Hf-O coordination bond vibration is interpreted as a signature of missing cluster defects, resulting from less-rigid charge-balancing monocarboxylate formate ions replacing the dicarboxylate linker molecule. This signature is hypothesized to be independent of the topology in which the defects appear. Missing linker defects in Zr-UiO-66 are characterized by infrared absorption spectroscopy by the quenching of C-C and C-H vibrational modes confined to the linker molecule. Together, Raman and infrared vibrational spectroscopies coupled with standard characterization techniques are employed to directly probe the nature of defects as well as offer new characterization tools for missing cluster defects in UiO-66.

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Polyethyleneimine-Modified UiO-66-NH2(Zr) Metal-Organic Frameworks: Preparation and Enhanced CO2 Selective Adsorption.

Project description:UiO-66-NH2, a zirconium-based functional metal-organic framework (MOF), was postsynthetically modified via Schiff base reaction between aldehyde groups in glutaraldehyde and amino groups in UiO-66-NH2 and CO2-preabsorbed polyethyleneimine (PEI). The resulting PEI-modified MOFs, abbreviated as PEIC@UiO, were characterized with 1H NMR, Fourier transform infrared, powder X-ray diffraction, Brunauer-Emmett-Teller, scanning electron microscopy, and thermogravimetric analysis and evaluated as CO2 adsorbents. In comparison with pristine UiO-66-NH2, the PEIC@UiO adsorbents have reduced specific surface area (7-150 m2/g) but maintained the same crystal structure. Particularly, the PEIC96@UiO adsorbent exhibited significantly improved CO2/N2 adsorption selectivity (48 vs 25) and higher CO2 adsorption capacity (3.2 vs 2.7 mmol/g). The adsorbent also displayed moderate desorption energy (68 kJ/mol CO2), superior moisture endurance, and recyclability, which are very desirable for practical applications.

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"Shake 'n Bake" Route to Functionalized Zr-UiO-66 Metal-Organic Frameworks.

Project description:We report a novel synthetic procedure for the high-yield synthesis of metal-organic frameworks (MOFs) with fcu topology with a UiO-66-like structure starting from a range of commercial ZrIV precursors and various substituted dicarboxylic linkers. The syntheses are carried out by grinding in a ball mill the starting reagents, namely, Zr salts and the dicarboxylic linkers, in the presence of a small amount of acetic acid and water (1 mL total volume for 1 mmol of each reagent), followed by incubation at either room temperature or 120 °C. Such a simple "shake 'n bake" procedure, inspired by the solid-state reaction of inorganic materials, such as oxides, avoids the use of large amounts of solvents generally used for the syntheses of Zr-MOF. Acidity of the linkers and the amount of water are found to be crucial factors in affording materials of quality comparable to that of products obtained under solvo- or hydrothermal conditions.

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Stability of Zr-Based UiO-66 Metal-Organic Frameworks in Basic Solutions.

Project description:Although Zr-based metal-organic frameworks (MOFs) exhibit robust chemical and physical stability in the presence of moisture and acidic conditions, their susceptibility to nucleophilic attacks from bases poses a critical challenge to their overall stability. Herein, we systematically investigate the stability of Zr-based UiO-66 (UiO = University of Oslo) MOFs in basic solutions. The impact of 11 standard bases, including inorganic salts and organic bases, on the stability of these MOFs is examined. The destruction of the framework is confirmed through powder X-ray diffraction (PXRD) patterns, and the monitored dissolution of ligands from the framework is assessed using nuclear magnetic resonance (NMR) spectroscopy. Our key findings reveal a direct correlation between the strength and concentration of the base and the destruction of the MOFs. The summarized data provide valuable insights that can guide the practical application of Zr-based UiO-66 MOFs under basic conditions, offering essential information for their optimal utilization in various settings.

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Modulator-free approach towards missing-cluster defect formation in Zr-based UiO-66.

Project description:By rigorous control of water, missing-cluster defects in Zr-based UiO-66 were generated to a remarkable extent without the need of acidic modulators. The presence of missing-cluster defects created hierarchical pore structures, which had a profound effect on the catalytic performance.

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Ultrathin hydrophobic films based on the metal organic framework UiO-66-COOH(Zr).

Project description:This work reports on the fabrication, optimization and characterization of ultrathin films containing submicrometer particles (sMPs) of the hydrophilic and water stable UiO-66-COOH(Zr) metal organic framework (MOF). MOF particles of ≈200 nm have been synthesized and assembled at the air-water interface by the Langmuir-Blodgett technique. The use of different solvents, mixtures of solvents and surfactants has been investigated in order to improve the stability of MOF dispersions and reduce particle aggregation. The compact MOF/surfactant films containing 10 wt % octadecylphoshonic acid (ODP) have been deposited on substrates of different nature by Langmuir-Blodgett (LB) and Langmuir-Schaefer (LS) methods, showing that the presence of even only one MOF/ODP monolayer can increase the water contact angle of highly hydrophilic substrates such as mica or glass up to 120°. These films were characterized by scanning electron microscopy, grazing incidence X-ray diffraction, Fourier transform infrared spectroscopy and atomic force microscopy, revealing the formation of a continuous film where ODP molecules adopt an almost vertical position and cover MOF particles. Moreover, the presence of MOF particles significantly enhances the surface roughness and allows ultrathin, hydrophobic coverage to be obtained. Finally, it has been shown that the crystallinity and the porosity of the MOF remains almost unaltered in MOF/ODP films.

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Project description:In this work, a bimetallic MOF UiO-66 Ce-Zr to degrade bisphenol A (BPA) in water was synthesised. The material exhibited a remarkable degradation efficiency of 84.3% under UV irradiation for 240 minutes. Combining cerium (Ce) and zirconium (Zr) in the MOF structure enhanced the catalytic activity and reinforced its structural stability. Comprehensive characterisation was performed using PXRD, FT-IR, SEM-EDS, XPS, and N₂ adsorption-desorption isotherms. Scavenger tests confirmed that hydroxyl (˙OH) and superoxide (˙O₂⁻) radicals played a crucial role in the photocatalysis. The material demonstrated excellent reusability, maintaining high performance over three cycles with minimal structural changes. Furthermore, a toxicological evaluation of the degradation by-products was conducted using UPLC-MS, reaffirming the potential of the material as an efficient water treatment system. This study underscores the potential of UiO-66 Ce-Zr as a stable and effective photocatalyst for water treatment applications, particularly in removing emerging pollutants such as BPA.

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Catalytic Advantages of SO3H-Modified UiO-66(Zr) Materials Obtained via Microwave Synthesis in Friedel-Crafts Acylation Reaction.

Project description:The catalytic activity and stability of sulfonic-based UiO-66(Zr) materials were tested in the Friedel-Crafts acylation of anisole with acetic anhydride. The materials were prepared using microwave-assisted synthesis, producing microporous materials with remarkable crystallinity and physicochemical features as acid catalysts. Different ratios between both organic ligands, terephthalic acid (H2BDC) and monosodium 2-sulfoterephthalic acid (H2BDC-SO3Na), were used for the synthesis to modulate the sulfonic content. The sulfonic-based UiO-66(Zr) material synthesized with a H2BDC/H2BDC-SO3Na molar ratio of 40/60 exhibited the best catalytic performance in the acidic-catalyzed Friedel-Crafts acylation reaction. This ratio balanced the number of sulfonic acid sites and their accessibility within the UiO-66 microporous structure. The catalytic performance of this material increased remarkably at 200 °C, outperforming reference acids and commercial heterogeneous catalysts such as Nafion-SAC-13 and Amberlyst-70. Additionally, the best sulfonic-based UiO-66(Zr) material proved to be stable in four successive reaction cycles, maintaining both its catalytic activity and its structural integrity.

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