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Towards new NIR dyes for free radical photopolymerization processes
The use of cheap and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 µm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is pr...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8381812/ https://www.ncbi.nlm.nih.gov/pubmed/34476013 http://dx.doi.org/10.3762/bjoc.17.133 |
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author | Mokbel, Haifaa Noirbent, Guillaume Gigmes, Didier Dumur, Frédéric Lalevée, Jacques |
author_facet | Mokbel, Haifaa Noirbent, Guillaume Gigmes, Didier Dumur, Frédéric Lalevée, Jacques |
author_sort | Mokbel, Haifaa |
collection | PubMed |
description | The use of cheap and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 µm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is proposed. Remarkably, 11 of them were never synthesized before. Markedly, noncharged structures, negatively charged cyanine bearing Na(+) as counter cation, and positively charged cyanines bearing (B(Ph)(4)(−)) or (I(−)) as counter anions were examined as promising NIR light photoinitiating systems. Excellent photoinitiating abilities were found for some reported dyes when used in combination with iodonium salt and amine. Markedly, photothermal effects with a huge heater behavior were also observed for different NIR dye structures. Interestingly, the synthesis of interpenetrating polymer networks (IPNs, e.g., for the polymerization of acrylate/epoxy monomer blends) can also be carried out upon NIR light with the proposed systems. |
format | Online Article Text |
id | pubmed-8381812 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-83818122021-09-01 Towards new NIR dyes for free radical photopolymerization processes Mokbel, Haifaa Noirbent, Guillaume Gigmes, Didier Dumur, Frédéric Lalevée, Jacques Beilstein J Org Chem Full Research Paper The use of cheap and safe near-infrared (NIR) light is still the subject of intense research efforts but remains a huge challenge due to the associated low photon energy (wavelength from 0.78 to 2.5 µm). In this study, a series of 17 NIR dyes mainly based on a well-established cyanine scaffold is proposed. Remarkably, 11 of them were never synthesized before. Markedly, noncharged structures, negatively charged cyanine bearing Na(+) as counter cation, and positively charged cyanines bearing (B(Ph)(4)(−)) or (I(−)) as counter anions were examined as promising NIR light photoinitiating systems. Excellent photoinitiating abilities were found for some reported dyes when used in combination with iodonium salt and amine. Markedly, photothermal effects with a huge heater behavior were also observed for different NIR dye structures. Interestingly, the synthesis of interpenetrating polymer networks (IPNs, e.g., for the polymerization of acrylate/epoxy monomer blends) can also be carried out upon NIR light with the proposed systems. Beilstein-Institut 2021-08-16 /pmc/articles/PMC8381812/ /pubmed/34476013 http://dx.doi.org/10.3762/bjoc.17.133 Text en Copyright © 2021, Mokbel et al. https://creativecommons.org/licenses/by/4.0/https://www.beilstein-journals.org/bjoc/terms/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). Please note that the reuse, redistribution and reproduction in particular requires that the author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) |
spellingShingle | Full Research Paper Mokbel, Haifaa Noirbent, Guillaume Gigmes, Didier Dumur, Frédéric Lalevée, Jacques Towards new NIR dyes for free radical photopolymerization processes |
title | Towards new NIR dyes for free radical photopolymerization processes |
title_full | Towards new NIR dyes for free radical photopolymerization processes |
title_fullStr | Towards new NIR dyes for free radical photopolymerization processes |
title_full_unstemmed | Towards new NIR dyes for free radical photopolymerization processes |
title_short | Towards new NIR dyes for free radical photopolymerization processes |
title_sort | towards new nir dyes for free radical photopolymerization processes |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8381812/ https://www.ncbi.nlm.nih.gov/pubmed/34476013 http://dx.doi.org/10.3762/bjoc.17.133 |
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