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Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems

Diaryliodonium salts are well-established compounds in free radical chemistry and are already used as photoinitiators (free radical or cationic polymerization), but the presence of counter anions is a strong drawback. Indeed, a counter anion is always required (e.g., SbF(6)(−)) leading to potential...

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Autores principales: Kirschner, Julie, Paillard, Julien, Bouzrati-Zerelli, Mariem, Becht, Jean-Michel, Klee, Joachim E., Chelli, Saloua, Lakhdar, Sami, Lalevée, Jacques
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6719945/
https://www.ncbi.nlm.nih.gov/pubmed/31405210
http://dx.doi.org/10.3390/molecules24162913
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author Kirschner, Julie
Paillard, Julien
Bouzrati-Zerelli, Mariem
Becht, Jean-Michel
Klee, Joachim E.
Chelli, Saloua
Lakhdar, Sami
Lalevée, Jacques
author_facet Kirschner, Julie
Paillard, Julien
Bouzrati-Zerelli, Mariem
Becht, Jean-Michel
Klee, Joachim E.
Chelli, Saloua
Lakhdar, Sami
Lalevée, Jacques
author_sort Kirschner, Julie
collection PubMed
description Diaryliodonium salts are well-established compounds in free radical chemistry and are already used as photoinitiators (free radical or cationic polymerization), but the presence of counter anions is a strong drawback. Indeed, a counter anion is always required (e.g., SbF(6)(−)) leading to potential toxicity issues or release of HF. In the present paper, counter anion-free and fluoride-free aryliodonium salts are proposed, that is, aryliodonium ylides (AY) are studied here as new and efficient additives for radical chemistry and an example is provided for the camphorquinone (CQ)/amine based photoinitiating systems (PISs) for the polymerization of thick (1.4 mm) and thin (20–13 µm) methacrylates under air and blue light irradiation. The newly proposed PISs, for example, CQ/amine/AY, presented excellent polymerization performances and good bleaching properties were obtained after polymerization. Real-time Fourier transform infrared spectroscopy (RT-FTIR) was used to monitor the photopolymerization profiles. The chemical mechanisms involved were investigated using electron spin resonance (ESR).
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spelling pubmed-67199452019-09-10 Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems Kirschner, Julie Paillard, Julien Bouzrati-Zerelli, Mariem Becht, Jean-Michel Klee, Joachim E. Chelli, Saloua Lakhdar, Sami Lalevée, Jacques Molecules Article Diaryliodonium salts are well-established compounds in free radical chemistry and are already used as photoinitiators (free radical or cationic polymerization), but the presence of counter anions is a strong drawback. Indeed, a counter anion is always required (e.g., SbF(6)(−)) leading to potential toxicity issues or release of HF. In the present paper, counter anion-free and fluoride-free aryliodonium salts are proposed, that is, aryliodonium ylides (AY) are studied here as new and efficient additives for radical chemistry and an example is provided for the camphorquinone (CQ)/amine based photoinitiating systems (PISs) for the polymerization of thick (1.4 mm) and thin (20–13 µm) methacrylates under air and blue light irradiation. The newly proposed PISs, for example, CQ/amine/AY, presented excellent polymerization performances and good bleaching properties were obtained after polymerization. Real-time Fourier transform infrared spectroscopy (RT-FTIR) was used to monitor the photopolymerization profiles. The chemical mechanisms involved were investigated using electron spin resonance (ESR). MDPI 2019-08-11 /pmc/articles/PMC6719945/ /pubmed/31405210 http://dx.doi.org/10.3390/molecules24162913 Text en © 2019 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
Kirschner, Julie
Paillard, Julien
Bouzrati-Zerelli, Mariem
Becht, Jean-Michel
Klee, Joachim E.
Chelli, Saloua
Lakhdar, Sami
Lalevée, Jacques
Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title_full Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title_fullStr Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title_full_unstemmed Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title_short Aryliodonium Ylides as Novel and Efficient Additives for Radical Chemistry: Example in Camphorquinone (CQ)/Amine Based Photoinitiating Systems
title_sort aryliodonium ylides as novel and efficient additives for radical chemistry: example in camphorquinone (cq)/amine based photoinitiating systems
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6719945/
https://www.ncbi.nlm.nih.gov/pubmed/31405210
http://dx.doi.org/10.3390/molecules24162913
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