The first solid state porphyrin-weak acid molecular complex: A novel metal free, nanosized and porous photocatalyst for large scale aerobic oxidations in water

Heydari-turkmani, Akram; Zakavi, Saeed

doi:10.1016/j.jcat.2018.06.011

Cited by 30 publications

(42 citation statements)

References 62 publications

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“…In 2018, Zakavi reported the synthesis of a porphyrincarboxylic acid catalyst and its immobilization on nanoparticles for the aerobic oxidation of thioanisole derivatives and an aliphatic sulfide in aqueous media under white LED irradiation (Table 7, entry 5). [62] Recently, in 2020, Ye and coworkers proposed the use of bismuth oxyhalides in photocatalytic processes for water treatment, used Bi 4 O 5 Br 2 as the catalyst and water as the solvent to photochemically oxidize alkyl-aryl sulfides (Table 7, entry 6). [63] Mechanistic investigations indicate that superoxide radical anion is involved in the oxidation process.…”

Section: Nanoparticles-miscellaneousmentioning

confidence: 99%

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Aerobic Photocatalysis: Oxidation of Sulfides to Sulfoxides

2022

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Sulfoxides constitute one of the most important functional groups in organic chemistry found in numerous pharmaceuticals and natural products. Sulfoxides are usually obtained from the oxidation of the corresponding sulfides. Among various oxidants, oxygen or air are considered the greenest and most sustainable reagent. Photochemistry and photocatalysis is increasingly applied in new, as well as traditional, yet demanding, reaction, like the aerobic oxidation of sulfides to sulfoxides, since photocatalysis has provided the means to access them in mild and effective ways. In this review, we will summarize the photochemical protocols that have been developed for the oxidation of sulfides to sulfoxides, employing air or oxygen as the oxidant. The aim of this review is to present: i) a historical overview, ii) the key mechanistic studies and proposed mechanisms and iii) categorize the different catalytic systems in literature.Scheme 2. Traditional sulfide oxidation methods. Scheme 3. Sulfide oxidation methods utilizing oxygen as the oxidant.

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Section: Nanoparticles-miscellaneousmentioning

confidence: 99%

“…In 2018, Zakavi reported the synthesis of a porphyrin‐carboxylic acid catalyst and its immobilization on nanoparticles for the aerobic oxidation of thioanisole derivatives and an aliphatic sulfide in aqueous media under white LED irradiation (Table 7, entry 5) [62] …”

Section: Heterogeneous Photocatalysismentioning

confidence: 99%

Aerobic Photocatalysis: Oxidation of Sulfides to Sulfoxides

2022

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“…Nanoparticles of Amberlyst 15 (nanoAmbSO 3 H) and its sodium salt (nanoAmbSO 3 Na) were prepared and characterized according to the previous report. 17,18 2.5. Immobilization of H 2 TMPyP(BF 3 ) 2 on NanoAmbSO 3 Na.…”

Section: Methodsmentioning

confidence: 99%

“…46 The procedure was described elsewhere. [10][11][12][13][17][18][19]41 3. RESULTS AND DISCUSSION 3.1.…”

Section: Methodsmentioning

confidence: 99%

Significantly Increased Stability of Donor–Acceptor Molecular Complexes under Heterogeneous Conditions: Synthesis, Characterization, and Photosensitizing Activity of a Nanostructured Porphyrin–Lewis Acid Adduct

Mojarrad

Zakavi

2020

ACS Appl. Mater. Interfaces

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While the BF 3 complexes of meso-tetra(aryl)porphyrins are readily decomposed into their components under aqueous conditions, immobilization of meso-tetrakis(N-methylpyridinium-4-yl)porphyrin (H 2 TMPyP) on a nanosized polymer (sodium salt of Amberlyst 15, nanoAmbSO 3 Na) formed a waterstable BF 3 complex applicable for efficient aerobic photooxidation of 1,5-dihydroxylnaphthalene and sulfides under green conditions. NanoAmbSO 3 @H 2 TMPyP(BF 3 ) 2 was characterized by diffuse reflectance UV−vis spectroscopy, dynamic light scattering, thermal gravimetric analysis, Brunauer−Emmett−Teller analysis, Fourier transform infrared spectroscopy, field emission scanning electron microscopy, and energy-dispersive X-ray spectroscopy techniques. The catalyst was successfully used for 10 consecutive reactions with no detectable degradation of the complex and decrease in the catalyst activity. NanoAmbSO 3 @H 2 TMPyP(BF 3 ) 2 was also completely stable toward dissociation to its components under different light conditions in acetonitrile. The singlet oxygen quantum yields φ Δ of H 2 TMPyP, nanoAmbSO 3 @H 2 TMPyP, and their molecular complexes with BF 3 , determined chemically by using 1,3diphenylisobenzofuran, revealed substantially higher values in the case of the heterogenized porphyrin and molecular complex.

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“…Recycling of the methylene blue-dyed polyester fabrics and 99 was not carried out, while 98 was recovered and reused three times, with a slight decrease in its activity at the third catalytic cycle. In addition, two C60-BODIPY photosensitizers (C60-B1/C60-B2, 100a,b) [227], a C70-BODIPY-triphenylamine triad (C70-B-T, 101) [228] and a meso-tetrakis(N-methylpyridinium-4-yl)porphyrin supported on the sodium salt of Amberlyst 15 nanoparticles and complexed with formic acid (nanoAmbSO3@H2TYMPyP(HCO2H)2, 102a) [229] and BF3 (nanoAmbSO3@H2TYMPyP(BF3)2, 102b) [230] were employed in the mentioned transformation, obtaining Juglone (85, R 1 = R 2 = R 5 = H, R 4 = OH) in high yield (only quantum yield was given in the case of using 100 and 101) (Figure 31). The recyclability of 100 and 101 was not tested, while 102a and 102b were recycled but in a different photo-oxidation reaction.…”

Section: Heterogeneous Oxidative Dehydrogenation Of C-o Bondmentioning

confidence: 99%

Visible Light-Induced Aerobic Oxidative Dehydrogenation of C–N/C–O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments

Torregrosa-Chinillach

Chinchílla

2022

Molecules

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Performing synthetic transformation using visible light as energy source, in the presence of a photocatalyst as a promoter, is currently of high interest, and oxidation reactions carried out under these conditions using oxygen as the final oxidant are particularly convenient from an environmental point of view. This review summarizes the recent developments achieved in the oxidative dehydrogenation of C–N and C–O bonds, leading to C=N and C=O bonds, respectively, using air or pure oxygen as oxidant and metal-free homogeneous or recyclable heterogeneous photocatalysts under visible light irradiation.

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The first solid state porphyrin-weak acid molecular complex: A novel metal free, nanosized and porous photocatalyst for large scale aerobic oxidations in water

Cited by 30 publications

References 62 publications

Aerobic Photocatalysis: Oxidation of Sulfides to Sulfoxides

Aerobic Photocatalysis: Oxidation of Sulfides to Sulfoxides

Significantly Increased Stability of Donor–Acceptor Molecular Complexes under Heterogeneous Conditions: Synthesis, Characterization, and Photosensitizing Activity of a Nanostructured Porphyrin–Lewis Acid Adduct

Visible Light-Induced Aerobic Oxidative Dehydrogenation of C–N/C–O to C=N/C=O Bonds Using Metal-Free Photocatalysts: Recent Developments

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