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901111

Sigma-Aldrich

Phenox O-PC™ A0202

New Iridium, ≥97%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C46H31NO
Numero CAS:
1987900-95-7
Peso molecolare:
613.74
Codice UNSPSC:
12161600
NACRES:
NA.22

Livello qualitativo

100

Saggio

≥97%

Forma fisica

powder or crystals

Impiego in reazioni chimiche

reagent type: catalyst
reaction type: Photocatalysis

Punto di fusione

171 °C

Attivazione fotocatalizzatore

400 nm

Stringa SMILE

C1(C=CC(C2=CC=C(C3=CC=CC=C3)C=C2)=C4)=C4OC(C=C(C5=CC=C(C6=CC=CC=C6)C=C5)C=C7)=C7N1C8=C(C=CC=C9)C9=CC=C8

Applicazioni

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.

Product can be used with our line of photoreactors: Including Penn PhD (Z744035) & SynLED 2.0 (Z744080)

Altre note

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

Note legali

Patent application PCT/US2016/058245. Sold in collaboration with New Iridium Inc. For orders greater than 25g, please contact New Iridium at chern@newiridium.com or visit https://www.newiridium.com.
Phenox O-PC is a trademark of New Iridium LLC

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Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts.
Pearson, et al.
Journal of the American Chemical Society, 138, 11399-11407 (2017)
Ya Du et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(46), 10962-10968 (2017-06-28)
Photoredox catalysis is a versatile approach for the construction of challenging covalent bonds under mild reaction conditions, commonly using photoredox catalysts (PCs) derived from precious metals. As such, there is need to develop organic analogues as sustainable replacements. Although several
Jordan C Theriot et al.
Science (New York, N.Y.), 352(6289), 1082-1086 (2016-04-02)
Atom transfer radical polymerization (ATRP) has become one of the most implemented methods for polymer synthesis, owing to impressive control over polymer composition and associated properties. However, contamination of the polymer by the metal catalyst remains a major limitation. Organic
Chern-Hooi Lim et al.
Journal of the American Chemical Society, 139(1), 348-355 (2016-12-16)
Photoexcited intramolecular charge transfer (CT) states in N,N-diaryl dihydrophenazine photoredox catalysts are accessed through catalyst design and investigated through combined experimental studies and density functional theory (DFT) calculations. These CT states are reminiscent of the metal to ligand charge transfer
Ryan M Pearson et al.
Journal of the American Chemical Society, 138(35), 11399-11407 (2016-08-25)
N-Aryl phenoxazines have been synthesized and introduced as strongly reducing metal-free photoredox catalysts in organocatalyzed atom transfer radical polymerization for the synthesis of well-defined polymers. Experiments confirmed quantum chemical predictions that, like their dihydrophenazine analogs, the photoexcited states of phenoxazine
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Articoli

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

Photoredox catalysis is a powerful synthetic methodology to form challenging covalent bonds using light irradiation. It is effective for light-driven polymer and small molecule synthesis.

Contenuto correlato

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