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Michler's Ketone as an Interesting Scaffold for the Design of High‐Performance Dyes in Photoinitiating Systems Upon Visible Light
Author(s) -
Mokbel Haifaa,
Dumur Frédéric,
Graff Bernadette,
Mayer Cédric R.,
Gigmes Didier,
Toufaily Joumana,
Hamieh Tayssir,
Fouassier JeanPierre,
Lalevée Jacques
Publication year - 2014
Publication title -
macromolecular chemistry and physics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.57
H-Index - 112
eISSN - 1521-3935
pISSN - 1022-1352
DOI - 10.1002/macp.201300779
Subject(s) - photochemistry , polymerization , polymer , fluorescence , acceptor , materials science , electron paramagnetic resonance , electron acceptor , visible spectrum , photodissociation , chemistry , optoelectronics , optics , nuclear magnetic resonance , physics , condensed matter physics , composite material
Four new push–pull dyes derived from Michler's ketones are investigated. These dyes, based on a donor–π–acceptor (D–π–A) structure, exhibit a tunable character according to the electron‐withdrawing ability of the acceptor used. The new proposed structures can be used in high‐performance photoinitiating systems. Remarkably, two of them are characterized by an excellent reactivity to initiate the free‐radical polymerization of acrylates, the ring‐opening polymerization of epoxides, as well as the synthesis of interpenetrating polymer networks (IPNs) under exposure to a laser diode at 457 nm. The chemical mechanisms are investigated by steady‐state photolysis, fluorescence, and electron spin‐resonance (ESR) experiments.