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Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing

Radical chemistry is a very convenient way to produce polymer materials. Here, an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical pol...

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Autores principales: Al Mousawi, Assi, Garra, Patxi, Dumur, Frédéric, Bui, Thanh-Tuan, Goubard, Fabrice, Toufaily, Joumana, Hamieh, Tayssir, Graff, Bernadette, Gigmes, Didier, Fouassier, Jean Pierre, Lalevée, Jacques
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149745/
https://www.ncbi.nlm.nih.gov/pubmed/29207574
http://dx.doi.org/10.3390/molecules22122143
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author Al Mousawi, Assi
Garra, Patxi
Dumur, Frédéric
Bui, Thanh-Tuan
Goubard, Fabrice
Toufaily, Joumana
Hamieh, Tayssir
Graff, Bernadette
Gigmes, Didier
Fouassier, Jean Pierre
Lalevée, Jacques
author_facet Al Mousawi, Assi
Garra, Patxi
Dumur, Frédéric
Bui, Thanh-Tuan
Goubard, Fabrice
Toufaily, Joumana
Hamieh, Tayssir
Graff, Bernadette
Gigmes, Didier
Fouassier, Jean Pierre
Lalevée, Jacques
author_sort Al Mousawi, Assi
collection PubMed
description Radical chemistry is a very convenient way to produce polymer materials. Here, an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides utilizing Light Emitting Diodes LEDs @405 nm. Excellent polymerization-initiating abilities are found and high final reactive function conversions are obtained. Interestingly, these new derivatives display much better near-UV polymerization-initiating abilities compared to a reference UV absorbing carbazole (CARET 9H-carbazole-9-ethanol) demonstrating that the new substituents have good ability to red shift the absorption of the proposed photoinitiators. All the more strikingly, in combination with iodonium salt, Cd1–Cd7 are likewise preferred as cationic photoinitiators over the notable photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO) for mild irradiation conditions featuring their remarkable reactivity. In particular their utilization in the preparation of new cationic resins for LED projector 3D printing is envisioned. A full picture of the included photochemical mechanisms is given.
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spelling pubmed-61497452018-11-13 Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing Al Mousawi, Assi Garra, Patxi Dumur, Frédéric Bui, Thanh-Tuan Goubard, Fabrice Toufaily, Joumana Hamieh, Tayssir Graff, Bernadette Gigmes, Didier Fouassier, Jean Pierre Lalevée, Jacques Molecules Article Radical chemistry is a very convenient way to produce polymer materials. Here, an application of a particular photoinduced radical chemistry is illustrated. Seven new carbazole derivatives Cd1–Cd7 are incorporated and proposed as high performance near-UV photoinitiators for both the free radical polymerization (FRP) of (meth)acrylates and the cationic polymerization (CP) of epoxides utilizing Light Emitting Diodes LEDs @405 nm. Excellent polymerization-initiating abilities are found and high final reactive function conversions are obtained. Interestingly, these new derivatives display much better near-UV polymerization-initiating abilities compared to a reference UV absorbing carbazole (CARET 9H-carbazole-9-ethanol) demonstrating that the new substituents have good ability to red shift the absorption of the proposed photoinitiators. All the more strikingly, in combination with iodonium salt, Cd1–Cd7 are likewise preferred as cationic photoinitiators over the notable photoinitiator bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (BAPO) for mild irradiation conditions featuring their remarkable reactivity. In particular their utilization in the preparation of new cationic resins for LED projector 3D printing is envisioned. A full picture of the included photochemical mechanisms is given. MDPI 2017-12-04 /pmc/articles/PMC6149745/ /pubmed/29207574 http://dx.doi.org/10.3390/molecules22122143 Text en © 2017 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Al Mousawi, Assi
Garra, Patxi
Dumur, Frédéric
Bui, Thanh-Tuan
Goubard, Fabrice
Toufaily, Joumana
Hamieh, Tayssir
Graff, Bernadette
Gigmes, Didier
Fouassier, Jean Pierre
Lalevée, Jacques
Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title_full Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title_fullStr Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title_full_unstemmed Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title_short Novel Carbazole Skeleton-Based Photoinitiators for LED Polymerization and LED Projector 3D Printing
title_sort novel carbazole skeleton-based photoinitiators for led polymerization and led projector 3d printing
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6149745/
https://www.ncbi.nlm.nih.gov/pubmed/29207574
http://dx.doi.org/10.3390/molecules22122143
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