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Key Documents

901112

Sigma-Aldrich

PhenN O-PC B0301

New Iridium, ≥97%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C32H22N2
Numéro CAS:
Poids moléculaire :
434.53
Code UNSPSC :
12161600
Nomenclature NACRES :
NA.22

Niveau de qualité

Pureté

≥97%

Forme

powder or crystals

Pertinence de la réaction

reagent type: catalyst
reaction type: Photocatalysis

Activation du photocatalyseur

460 nm

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)

Informations légales

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Pictogrammes

Exclamation mark

Mention d'avertissement

Warning

Mentions de danger

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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
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
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
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

Articles

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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