Fe3O4 Nanoparticles: A Robust and Magnetically Recoverable Catalyst for Direct C‐H Bond Selenylation and Sulfenylation of Benzothiazoles

Rafique, Jamal; Saba, Sumbal; Frizon, Tiago Elias Allievi; Braga, Antônio L.

doi:10.1002/slct.201702623

Cited by 40 publications

(14 citation statements)

References 82 publications

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“…As part of our continued involvement in the chemistry of Nheterocycles (Saba et al, 2015(Saba et al, , 2016(Saba et al, , 2017(Saba et al, , 2018(Saba et al, , 2020Rafique et al, 2016Rafique et al, , 2018aSilva et al, 2017;Bettanin et al, 2018;Peterle et al, 2018;Rodigues et al, 2018;Tornquist et al, 2018;Meirinho et al, 2019;Neto et al, 2020;Scheide et al, 2020) and material sciences (Frizon et al, 2014(Frizon et al, , 2015(Frizon et al, , 2016(Frizon et al, , 2018Bo et al, 2016Bo et al, , 2018Westrup et al, 2016;Matzkeit et al, 2018;Regis et al, 2018), herein, we report the synthesis and characterization of BOX derivatives containing electrondonor groups (alkylated tetrazole rings) connected to the 2,1,3-BOX group as an electron-acceptor unit. In addition, thermal, electrochemical, and theoretical predictions were made and photophysical analysis was performed to study the stability, likely geometry, and luminescence properties of these compounds in their ground and excited electronic states.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

et al. 2020

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Herein, we report the synthesis and characterization of fluorophores containing a 2,1,3-benzoxadiazole unit associated with a π-conjugated system (D-π-A-π-D). These new fluorophores in solution exhibited an absorption maximum at around ∼419 nm (visible region), as expected for electronic transitions of the π-π * type (ε ∼2.7 × 10 7 L mol −1 cm −1), and strong solvent-dependent fluorescence emission (Φ FL ∼0.5) located in the bluish-green region. The Stokes' shift of these compounds is ca. 3,779 cm −1 , which was attributed to an intramolecular charge transfer (ICT) state. In CHCl 3 solution, the compounds exhibited longer and shorter lifetimes, which was attributed to the emission of monomeric and aggregated molecules, respectively. Density functional theory was used to model the electronic structure of the compounds 9a-d in their excited and ground electronic states. The simulated emission spectra are consistent with the experimental results, with different solvents leading to a shift in the emission peak and the attribution of a π-π * state with the characteristics of a charge transfer excitation. The thermal properties were analyzed by thermogravimetric analysis, and a high maximum degradation rate occurred at around 300 • C. Electrochemical studies were also performed in order to determine the band gaps of the molecules. The electrochemical band gaps (2.48-2.70 eV) showed strong correlations with the optical band gaps (2.64-2.67 eV).

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Section: Introductionmentioning

confidence: 99%

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

et al. 2020

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“…In this regard, a number of papers have pointed out the synthetic versatility of compounds termed organochalcogens [6][7][8][9][10][11][12][13]. Selenium-containing organochalcogenides seems to be of great therapeutic relevance, mostly due to the ability of these compounds to mimic natural substances with antioxidant, antitumor, antimicrobial and antiviral activities [14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Frizon¹,

Cararo²,

Saba³

et al. 2020

Preprint

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Herein we report the synthesis of novel selenocyanates and assessment of their effect on the oxidative challenge elicited by hydrogen peroxide (H2O2) in cultured mouse neurons. First, α-methylene-β-hydroxy esters were prepared as precursors of allylic bromides. A reaction involving the generated bromides and sodium selenocyanate was conducted to produce the desired selenocyanates (3a-f). We next prepared cultures of neurons from 7-day-old-mice (n = 36). H2O2 (10⁻5 M) was added into the culture flasks as an oxidative stress inducer, alone or combined with one of each designed compounds. PhSe)2 was used as positive control. It was carried out assessment of lipid (thiobarbituric acid reactive species, 4-hydroxy-2’-nonenal, 8-isoprostane), DNA (8-hydroxy-2’-deoxyguanosine) and protein (carbonyl) modification parameters. Finally, catalase and superoxide dismutase activities were also evaluated. Among the compounds, 3b, 3d and 3f exhibited the most pronounced pattern of antioxidant activity, similar to (PhSe)2. These novel aromatic selenocyanates could be promising to be tried in most sophisticated in vitro studies or even at preclinical level.

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“…The integration of nanotechnology with green chemistry offers innovative prospects to meet current demand for ecological and economic sustainability . MNPs based magnetically retrievable catalysis has received considerable attention in synthetic chemistry . However, despite substantial progress, Research was conducted to create magnetically recoverable organcatalysts.…”

Section: Introductionmentioning

confidence: 99%

Copper‐Phosphine Supported Fe₃O₄@SiO₂ as a Novel Reusable Nanocatalyst‐Catalyzed Tandem Reaction of Indole and Alcohols to Bis(indolyl)methanes under Blue LED Light

Mohammadi

Shaterian

2019

ChemistrySelect

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Nano Fe3O4@SiO2@TPP−Cu as a novel heterogeneous nanocatalyst was prepared and authenticated by usual analytical and spectroscopic techniques. The prepared Fe3O4@SiO2@TPP−Cu was applied to preparation of bis(indolyl)methane derivatives via a three‐component reaction of aromatic alcohols with indoles under blue led lights. The advantages of this method are the selective oxidation of alcohols under mild conditions. In addition, the recycling studies revealed that catalyst could be easily recovered using an external magnet and reused for five times without significant loss of its catalytic activity.

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Fe₃O₄ Nanoparticles: A Robust and Magnetically Recoverable Catalyst for Direct C‐H Bond Selenylation and Sulfenylation of Benzothiazoles

Cited by 40 publications

References 82 publications

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Copper‐Phosphine Supported Fe₃O₄@SiO₂ as a Novel Reusable Nanocatalyst‐Catalyzed Tandem Reaction of Indole and Alcohols to Bis(indolyl)methanes under Blue LED Light

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Fe3O4 Nanoparticles: A Robust and Magnetically Recoverable Catalyst for Direct C‐H Bond Selenylation and Sulfenylation of Benzothiazoles

Cited by 40 publications

References 82 publications

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

Synthesis of 2,1,3-Benzoxadiazole Derivatives as New Fluorophores—Combined Experimental, Optical, Electro, and Theoretical Study

Synthesis of Novel Selenocyanates and Evaluation of Their Effect in Cultured Mouse Neurons Submitted to Oxidative Stress

Copper‐Phosphine Supported Fe3O4@SiO2 as a Novel Reusable Nanocatalyst‐Catalyzed Tandem Reaction of Indole and Alcohols to Bis(indolyl)methanes under Blue LED Light

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Fe₃O₄ Nanoparticles: A Robust and Magnetically Recoverable Catalyst for Direct C‐H Bond Selenylation and Sulfenylation of Benzothiazoles

Copper‐Phosphine Supported Fe₃O₄@SiO₂ as a Novel Reusable Nanocatalyst‐Catalyzed Tandem Reaction of Indole and Alcohols to Bis(indolyl)methanes under Blue LED Light