LED and visible light-induced metal free ATRP using reducible dyes in the presence of amines

Abstract

A new photoinitiating system involving electron acceptor dyes, namely, eosin Y and erythrosin B, in conjunction with alkyl halides and amines for photoinduced ATRP of (meth)acrylates and vinyl monomers in the absence of inorganic catalysts is reported.

Nahinfrarot‐sensibilisierte photoinduzierte ATRP mit einer Kupfer(II)‐Katalysatorkonzentration im ppm‐Bereich

“…Verschiedene Herangehensweisen wurden vorgeschlagen und erfolgreich eingesetzt, um die Katalysatorkonzentration zu reduzieren, wie die Verwendung von Reduktionsmitteln, [2] die Entwicklung komplexer Katalysatorsysteme [3] und elektrochemische Versuchsanordnungen. [4] Photochemische Methoden einschließlich einer direkten Bestrahlung [5] und des Einsatzes verschiedener Sensibilisatoren, [6] Farbstoffe, [6,7] Nanopartikel [8] und porçser Materialien ergaben eine vielversprechende Reduzierung der Menge an Cu-Katalysatoren, die fürA TRP bençtigt werden. Das System wurde auch fürK lick-Reaktionen mit photochemischer Reduktion von Cu II zu Cu I angepasst.…”

Living Cationic Polymerization of Vinyl Ethers through a Photoinduced Radical Oxidation/Addition/Deactivation Sequence

“…Various photoactive compounds, such as photoinitiators, [8] dyes, [9] mesoporous structures, [10] and nanoparticles, [11] have been successfully employed the electron transfer and reduction of Cu II to Cu I , which in turn catalyzes the ATRP process. [14] It was recently demonstrated that the photoinduced ATRP method can also be applied in completely organic systems by using phenothiazines [15] and dyes [16] as photoreductants. [12] Photoinduced electron-transfer-promoted ATRP has also been reported for Ir(ppy) 3 -based systems by Hawker and co-workers.…”

“…Poly(vinyl ether) chains are then grown through successive photoinduced radical oxidation/addition/deactivation (PROAD) in a controlled manner. [14] It was recently demonstrated that the photoinduced ATRP method can also be applied in completely organic systems by using phenothiazines [15] and dyes [16] as photoreductants. [4] In recent years, there has been tremendous interest in developing new controlled/living polymerization (CLP) methods, involving almost all modes of polymerization processes.…”

“…Most of these approaches are based on photoinduced electron-transfer reactions. [14] It was recently demonstrated that the photoinduced ATRP method can also be applied in completely organic systems by using phenothiazines [15] and dyes [16] as photoreductants. A similar photoinduced redox strategy has been applied to azide-alkyne click reactions, which also utilize Cu I species.…”

Photoinitiated Metal Free Living Radical and Cationic Polymerizations

“…Another strategy involves the application of conventional Type II photoinitiators and certain dyes in conjunction with amines as electron sources and alkyl halides as initiators [33][34][35]. In this particular case, the mechanism of radical formation occurs by a reductive quenching mechanism.…”