Oxidation of alkyl benzenes by a flavin photooxidation catalyst on nanostructured metal-oxide films

Dongare, Prateek; Mackenzie, Ian A.; Wang, Degao; Nicewicz, David A.; Meyer, Thomas J.

doi:10.1073/pnas.1707318114

Cited by 37 publications

(15 citation statements)

References 42 publications

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“…As a mild, efficient, and environmentally friendly approach it has the potential to unlock unique reactions that are previously inaccessible under thermal conditions. Significant advances were made for the oxidation of benzylic alcohols by using metal-based photocatalysts [38][39][40][41][42][43][44][45][46] and metal-free photocatalysis [47][48][49][50][51][52][53] in combination with various oxidants, such as TBHP and DDQ [54,55]. However, the reported methods require either specific nanoparticle catalysts [39][40][41][42] or the catalytic method is limited to electron-rich or electronneutral benzylic alcohols [56].…”

Section: Introductionmentioning

confidence: 99%

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

Yedase¹,

Kumar²,

Stahl³

et al. 2021

Beilstein J. Org. Chem.

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Section: Introductionmentioning

confidence: 99%

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

Yedase¹,

Kumar²,

Stahl³

et al. 2021

Beilstein J. Org. Chem.

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“…The hybrid catalytic system is efficient, easy to prepare, and separate from the solution, and can be successfully used in the removal of water-polluting dyes. Some examples of the flavin-conjugated metal-oxide surface such as TiO2 and BiOCl have been reported, but not applied to the degradation of complex molecules, such as AMT, and to the best of our knowledge, none demonstrated both the reduction and the oxidation of the substrates as presented within this paper [33][34][35].…”

Section: Introductionmentioning

confidence: 85%

Flavin-Conjugated Iron Oxide Nanoparticles as Enzyme-Inspired Photocatalysts for Azo Dye Degradation

2020

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In this work, a new photocatalytic system consisting of iron oxide nanoparticles (IONPs), coated with a catechol-flavin conjugate (DAFL), is synthesized and explored for use in water remediation. In order to test the efficiency of the catalyst, the photodegradation of amaranth (AMT), an azo dye water pollutant, was performed under aerobic and anaerobic conditions, using either ethylenediaminetetraacetic acid (EDTA) or 2-(N-morpholino)ethanesulfonic acid (MES) as electron donors. Depending on the conditions, either dye photoreduction or photooxidation were observed, indicating that flavin-coated iron-oxide nanoparticles can be used as a versatile enzyme-inspired photocatalysts.

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“…181−183 An alternative approach is to photoinitiate the organic transformations within the pores of dye-sensitized mesoporous thin films. 184 With transparent conductive oxides (section 2.4.4), reducing and/or oxidizing equivalents can be photogenerated for oxidative or reductive catalysis. This approach minimizes reaction volumes, facilitates isolation of the desired products, and enables more facile reuse of the molecular photocatalysts/ sensitizers.…”

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Perspectives on Dye Sensitization of Nanocrystalline Mesoporous Thin Films

Sampaio

Schneider

et al. 2020

J. Am. Chem. Soc.

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Recent advances in our mechanistic understanding of dye-sensitized electron transfer reactions occurring at metal oxide interfaces are described. These advances were enabled by the advent of mesoporous thin films, comprised of anatase TiO 2 nanocrystallites, that are amenable to spectroscopic and electrochemical characterization in unprecedented molecular-level detail. The metal-to-ligand charge transfer (MLCT) excited states of Ru polypyridyl compounds serve as the dye sensitizers. Excited-state injection often occurs on ultrafast time scales with yields that can be tuned from unity to near zero through modification of the sensitizer or the electrolyte composition. Transport of the injected electron and the oxidized sensitizer (hole hopping) are both operative in the composite mechanism for charge recombination between the injected electron and the oxidized sensitizer. Sensitizers that contain a pendant electron donor, as well as core/shell SnO 2 /TiO 2 nanostructures, often prolong the lifetime of the injected electron and provide fundamental insights into adiabatic and nonadiabatic electron transfer mechanisms. Regeneration of the oxidized sensitizer by iodide is enhanced through halogen bonding, orbital pathways, and ion pairing. A substantial ∼10 MV cm −1 electric field is created by electron injection into TiO 2 nanocrystallites that induces ion migration, reports on the sensitizer dipole orientation, and (in some cases) reorients or flips the sensitizer. Dye-sensitized conductive oxides also promote long-lived charge separation with bias dependent kinetics that provide insights into the reorganization energies associated with electron and proton-coupled electron transfer in the electric double layer.

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Oxidation of alkyl benzenes by a flavin photooxidation catalyst on nanostructured metal-oxide films

Abstract: We describe here a surface-bound, oxide-based procedure for the photooxidation of a family of aromatic hydrocarbons by a phosphatebearing flavin mononucleotide (FMN) photocatalyst on high surface area metal-oxide films.flavin | excited state | photooxidation | oxide surface | alkyl benzene

Cited by 37 publications

References 42 publications

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

Flavin-Conjugated Iron Oxide Nanoparticles as Enzyme-Inspired Photocatalysts for Azo Dye Degradation

Perspectives on Dye Sensitization of Nanocrystalline Mesoporous Thin Films

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