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Visible Light Photoredox Catalysts
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What are Visible Light Photoredox Catalysts?
A photoreaction undergoes a particular molecular conversion to form a product that is not obtained by a thermal reaction. Recently, visible light induced photoreactions have been a trending area of development. A photoreaction under visible light does not require high energy UV light and the reactions occur under mild conditions to avoid forming unexpected by-products.
A photocatalyst working for both one-electron oxidation and reduction under visible light irradiation, the so-called "visible light photoredox catalyst", receives much attention, because there is possibility for use as a solar energy source.1) A reaction mediated by a photoredox catalyst particularly works simply, whereas a thermal reaction under coexistence of oxidizing and reducing reagents is normally hard to make work. The reaction cycle using a photoredox catalyst involves both oxidative and reductive pathways, thus it shows a "redox-neutral" mechanism overall.
Photoredox catalysis by oxidative and reductive pathways
The formation of radical species normally requires a photoirradiation, redox reactions, and thermal activation by supplying high energy. The research field of photocatalysis developed transition metal complex catalysts and organic catalysts to form radical species under mild conditions, such as irradiating with visible light.
Some ruthenium(II) polypyridyl complexes and iridium(III) phenylpyridyl complexes work as photoredox catalysts under irradiation of visible light.2) These transition metal complexes are useful photocatalysts because they can form a long-lived triplet-excited state under photoirradiation. A chemical modification of the coordinating ligands controls the redox potentials of the transition metal complexes.3) Metal-free organic catalysts have also been developed. Some acridinium compounds with a donor-acceptor structure can be photoredox catalysts because the excited state exhibits a long-lived charge separation by irradiating with visible light.4) In addition, eosin and xanthene dyes are also used as photoredox catalysts.5)
Transition metal photoredox catalysts
Transition metal-free photoredox catalysts
Recent progress in photoredox catalysis has been remarkable. Photoredox catalysts are used in a variety of organic synthesis reactions,6) and many new applications have been developed including the combination of photoredox and transition metal catalysis called metallaphotoredox,7) the electrochemically mediated photoredox catalysis,8) and the application to the hybrid of light-harvesting proteins and photoredox catalysts called biohybrids,9) have been recently reported.
Our Latest Visible Photoredox Catalysts
- B6451
- [Ir(dFCF3ppy)2-(5,5'-dCF3bpy)]PF6
- Ir(dF(CF3)ppy)2(d(CF3)bpy)]PF6 has a higher reduction potential than other typical Ir complexes and is more oxidizing in the excited state.10)
- X0083
- peri-Xanthenoxanthene
- peri-Xanthenoxanthene is also used for organocatalyzed atom transfer radical polymerization (O-ATRP), which can perform metal-free atom transfer radical polymerization, and photoinduced energy transfer-reversible addition-fragmentation chain transfer (PET-RAFT) polymerization.11,12)
Learn more.
Redox Potentials of Visible Light Photoredox Catalysts
Redox potential data (literature values) for our visible light redox catalysts are listed on the following linked page.
References
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- 1) Review: Synthetic applications of photoredox catalysis with visible light
- 2) Photoredox Catalysis with Visible Light
- 3) Review: Shining Light on Photoredox Catalysis: Theory and Synthetic Applications
- 4) Review: Organic synthetic transformations using organic dyes as photoredox catalysts
- 5) Review: Synthetic applications of eosin Y in photoredox catalysis
- 6) A Retrosynthetic Approach for Photocatalysis
- 7) Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis
- 8) Synthetic Photoelectrochemistry
- 9) A biohybrid strategy for enabling photoredox catalysis with low-energy light
- 10) Catalytic Carbocation Generation Enabled by the Mesolytic Cleavage of Alkoxyamine Radical Cations
- 11) Metal-free atom transfer radical polymerization with ppm catalyst loading under sunlight
- 12) Organocatalytic PET-RAFT polymerization with a low ppm of organic photocatalyst under visible light
Visible Light Photoredox CatalystsOrganic Photoredox Catalyst for O-ATRP and PET-RAFT PolymerizationPhenylphenothiazine (PTH) DerivativeHighly Active Visible Light Photoredox Organocatalyst: Acr-450Iridium Photoredox Catalyst with Highly Oxidizing Excited StateVisible Light Photoredox Organocatalyst for Carbon (sp3)-Heteroatom Bond FormationIodinated Fluorescein for Various Applications