Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Mokbel, Haifaa, Noirbent, Guillaume, Gigmes, Didier, Dumur, Frédéric, Lalevée, Jacques
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
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
_version_ 1783741435591262208
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
work_keys_str_mv AT mokbelhaifaa towardsnewnirdyesforfreeradicalphotopolymerizationprocesses
AT noirbentguillaume towardsnewnirdyesforfreeradicalphotopolymerizationprocesses
AT gigmesdidier towardsnewnirdyesforfreeradicalphotopolymerizationprocesses
AT dumurfrederic towardsnewnirdyesforfreeradicalphotopolymerizationprocesses
AT laleveejacques towardsnewnirdyesforfreeradicalphotopolymerizationprocesses