PhenN O-PC^™ B0301

Name: PhenN O-PC<SUP>™</SUP> B0301
Brand: ALDRICH
Price: 117.75 USD
Availability: InStock

≥97%, powder or crystals, New Iridium

Synonym(s):

Miyake polymerization organophotoredox catalyst, 5,10-Di(2-Naphthyl)-5,10-dihydrophenazine, PhenN_2Naph

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About This Item

Empirical Formula (Hill Notation):

C₃₂H₂₂N₂

CAS Number:

1934269-97-2

Molecular Weight:

434.53

MDL number:

MFCD31619182

UNSPSC Code:

12161600

NACRES:

NA.22

Key Documents

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Product Name

PhenN O-PC^™ B0301, New Iridium, ≥97%

Quality Level

100

assay

≥97%

form

powder or crystals

reaction suitability

reagent type: catalyst
reaction type: Photocatalysis

photocatalyst activation

460 nm

SMILES string

[n]3(c4c([n](c7c3cccc7)c5cc6c(cc5)cccc6)cccc4)c1cc2c(cc1)cccc2

InChI key

HPIOBCHPZVAATK-UHFFFAOYSA-N

Related Categories

Catalysts

Organocatalysts

Photocatalysts

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Show Differences

1 of 4

This Item	901111	904953	904767
Sigma-Aldrich 901112 PhenN O-PC^™ B0301	Sigma-Aldrich 901111 Phenox O-PC^™ A0202	Sigma-Aldrich 904953 [Ru(dtbbpy)₃](PF₆)₂	Sigma-Aldrich 904767 [Ru(phen)₃]Cl₂
reaction suitability reagent type: catalyst reaction type: Photocatalysis	reaction suitability reagent type: catalyst reaction type: Photocatalysis	reaction suitability -	reaction suitability -
assay ≥97%	assay ≥97%	assay ≥95%	assay ≥95%
form powder or crystals	form powder or crystals	form powder or crystals	form powder or crystals
Quality Level 100	Quality Level 100	Quality Level -	Quality Level -
photocatalyst activation 460 nm	photocatalyst activation 400 nm	photocatalyst activation -	photocatalyst activation -

Application

This dihydrophenazine-based organic photoredox catalyst (in addition to the dihydrophenazine catalyst 901111) 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)

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 in collaboration with New Iridium Inc. For orders greater than 25g, please contact New Iridium at [email protected] or visit https://www.newiridium.com.

PhenN O-PC is a trademark of New Iridium Inc.

Phenox O-PC is a trademark of New Iridium LLC

pictograms

GHS07

signalword

Warning

hcodes

H302

pcodes

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

MKCW6276

MKCR5961

MKCF3372

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

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

Organocatalyzed atom transfer radical polymerization driven by visible light.

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

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

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

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

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

Articles

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.

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PhenN O-PC™ B0301