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901111 Sigma-Aldrich

Phenoxazine PC A0202

≥97%

Synonym: 3,7-Di(4-biphenyl) 1-naphthalene-10-phenoxazine, 3,7-Di([1,1′-biphenyl]-4-yl)-10-(naphthalen-1-yl)-10H-phenoxazine, Miyake organophotoredox catalyst, PhenO_1Naph_Biph

  • CAS Number 1987900-95-7

  • Empirical Formula (Hill Notation) C46H31NO

  • Molecular Weight 613.74

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Properties

Related Categories Catalysis and Inorganic Chemistry, Chemical Synthesis, Other Catalysts, Photocatalysis
assay   ≥97%
form   powder or crystals
mp   171 °C
reaction suitability   reagent type: catalyst
reaction type: Photocatalysis

Description

Application

This phenoxazine-based organic photoredox catalyst (in addition to the dihydrophenazine catalyst 901112) was designed to be a strong excited-state reductant and possesses advanced photophysical and electrochemical properties, enabling it to serve as a sustainable replacement for ruthenium- or iridium-based photoredox catalysts. For example, dihydrophenazine and phenoxazine derivatives were demonstrated to replace ruthenium or iridium complexes in the application of photoredox-catalyzed atom transfer radical polymerization (ATRP) for controlled polymer synthesis and small molecule transformations such as trifluoromethylation, atom transfer radical addition, and dual Nickel/photoredox catalyzed C-N and C-S cross-couplings. Dihydrophenazine- and phenoxazine-based organic photoredox catalysts were introduced in collaboration with the Miyake Research Group.

Other Notes

Strongly Reducing Visible Light Organic Photoredox Catalysts as Sustainable Alternatives to Precious Metals

Organocatalyzed Atom Transfer Radical Polymerization Driven by Visible Light

Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts

Intramolecular Charge Transfer and Ion Pairing in N,N-Diaryl Dihydrophenazine Photoredox Catalysts for Efficient Organocatalyzed Atom Transfer Radical Polymerization

Legal Information

Patent application PCT/US2016/058245. Sold under license from the Regents of the University of Colorado.

Phenoxazine PC is a trademark of New Iridium LLC

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Garret Miyake Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Garret Miyake Group - Professor Product Portal
Keywords: Catalysis, Materials Science, Polymer science, Polymerization reactions, Radical polymerization

Reducing Organic Photoredox Catalysts for Visible Light-Driven Polymer and Small Molecule Synthesis

Photoredox catalysis has emerged as a powerful synthetic methodology to form challenging covalent bonds under mild reaction conditions using light irradiation. Recently, phenoxazine (901111) and dihy...
Keywords: Absorption, Catalysis, Cross couplings, Polymerization reactions, Radical polymerization

Peer-Reviewed Papers
15

References

Related Products

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Description

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901112 5,10-Di(2-Naphthyl)-5,10-dihydrophenazine, ≥97%
903167 10-Phenylphenothiazine, ≥95%

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