Single-molecule photoredox catalysis

Haimerl, Josef Michael; Ghosh, Indrajit; König, Burkhard; Vogelsang, Jan; Lupton, John M.

doi:10.1039/c8sc03860k

Cited by 49 publications

(59 citation statements)

References 53 publications

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“…The authors noted that PDI is “quite stable under the photocatalytic conditions” . Incorporation of PDI into a metal‐organic polymer was claimed to facilitate catalyst‐substrate interaction, which is in line with the view that such pre‐association can be important for the photoreaction of short‐lived radical‐anion excited states …”

Section: The Next Level: Reductive Excited‐state Quenching Followed Bsupporting

confidence: 66%

“…Using Rhodamine 6G (Rh‐6G) as the photocatalyst, preparative‐scale reactions of the type in Table , entry 1, become possible under continuous blue‐light irradiation, and a spectroscopic study supports the view that the mechanism in Figure can lead to such reactions, particularly under conditions in which photocatalysts and substrates are pre‐associated . In presence of excess DIPEA ( N , N ‐diisopropylethylamine), the fluorescent excited state of Rh‐6G is quenched reductively, and the resulting one‐electron reduced species (PC .− ) is formed.…”

Section: The Next Level: Reductive Excited‐state Quenching Followed Bmentioning

confidence: 93%

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Multi‐Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

2020

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The energy of visible photons and the accessible redox potentials of common photocatalysts set thermodynamic limits to photochemical reactions that can be driven by traditional visible‐light irradiation. UV excitation can be damaging and induce side reactions, hence visible or even near‐IR light is usually preferable. Thus, photochemistry currently faces two divergent challenges, namely the desire to perform ever more thermodynamically demanding reactions with increasingly lower photon energies. The pooling of two low‐energy photons can address both challenges simultaneously, and whilst multi‐photon spectroscopy is well established, synthetic photoredox chemistry has only recently started to exploit multi‐photon processes on the preparative scale. Herein, we have a critical look at currently developed reactions and mechanistic concepts, discuss pertinent experimental methods, and provide an outlook into possible future developments of this rapidly emerging area.

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Section: The Next Level: Reductive Excited‐state Quenching Followed Bsupporting

confidence: 66%

Section: The Next Level: Reductive Excited‐state Quenching Followed Bmentioning

confidence: 93%

Multi‐Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

2020

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“…New molecules and nanomaterials have been designed and employed for the efficient absorption and harvesting of the entire spectrum of solar energy. [7] The photothermal conversion of light energy is one of the conventional approaches to energyh arvesting. [6] Meanwhile,t he use of the electronics tructure of the photoexciteds tates of molecules or photogenerated species can be an alternative approacht oe ffectively harvest longer-wavelength regions.…”

Section: Introductionmentioning

confidence: 99%

“…However,s uch approaches using organic moleculesa re limited and demand further attention. [7] The photothermal conversion of light energy is one of the conventional approaches to energyh arvesting. [8] The significance of this approach is still growingo wing to the applications of photothermal energyi np hotocatalytic reactions, solar energyh arvesting, and photoacoustict heragnosis.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced Betaine Generation for Efficient Photothermal Energy Conversion

Sasikumar

Takano

Biju

2020

Chemistry A European J

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The conversion of solar energy to thermal, chemical, or electrical energya ttracts great attentioni nc hemistry and physics. There has been ac onsiderable effort for the efficient extraction of photons throughout the entires olar spectrum. In this work light energy was efficiently harvested by using al ong-lived betaine photogeneratedfrom an acridinium-based electron donor-acceptor dyad. The photothermal energy-conversion efficiency of the dyad is significantly enhanced by simultaneousi llumination with blue (420-440 nm) andy ellow (> 480 nm) light in comparison with the sum of the conversione fficiencies for individual illumination with blue or yellow light. The enhanced photothermal effect is due to the photogenerated betaine, which absorbs longer-wavelength light than the dyad, and thus the dyadbetaine combination is promising for efficient photothermal energyc onversion. The mechanismso fb etaine generation and energy conversiona re discussed on the basis of steadystate and transient spectral measurements.Supporting information and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…The reactions were much slower than those under typical photoredox catalysis conditions due to the low intensity of the excitation source. Similarly, Lupton et al [7] continuously monitored the fluorescence of a single immobilized organic photoredox catalyst in an examination of the consecutive photoelectron transfer [8] mechanism.Herein we examine in situ luminescence measurements as a direct, continuous probe of photoredox catalysis under typical synthetic reaction conditions. To demonstrate the approach, we selected the aerobic oxidation of anthracene in acetonitrile using the [Ru(bpy) 3 ] 2 + catalyst irradiated with blue light, based on the prior work by Fukuzumi et al [9] using an organic photocatalyst (Figure 1a).…”

mentioning

confidence: 99%

Catalyst Luminescence Exploited as an Inherent In Situ Probe of Photoredox Catalysis

et al. 2019

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The luminescence of commonly used photoredox catalysts offers a continuous inherent in situ probe of electron or energy transfer that can be monitored by photodetectors such as a CCD spectrometer or a digital camera. This approach was applied with complementary ex situ experiments to examine the aerobic oxidation of anthracene with tris(2,2′‐bipyridine)ruthenium(II) as the catalyst. The reaction results in the precipitation of an isometrically pure syn‐tetraepoxide not seen in prior studies when an organic photocatalyst was employed. Changes in the emission were observed not only upon electron/energy transfer quenching of the catalyst but also from the presence of particles (undissolved substrate and precipitated product). These features impart dissimilar spectral distributions that can be discriminated by their relative contributions to the RGB data of the digital images. The approach thus enables interrogation of multiple facets of the reaction for monitoring and optimization, and offers unique insight into the mechanisms of photoredox catalysis systems.

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Single-molecule photoredox catalysis

Abstract: Photocatalytic dehalogenation by a common dyestuff under aqueous conditions is driven by energy-additive absorption of two photons on the single-molecule level.

Cited by 49 publications

References 53 publications

Multi‐Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

Multi‐Photon Excitation in Photoredox Catalysis: Concepts, Applications, Methods

Photoinduced Betaine Generation for Efficient Photothermal Energy Conversion

Catalyst Luminescence Exploited as an Inherent In Situ Probe of Photoredox Catalysis

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