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Photopolymerization and 3D/4D applications using newly developed dyes: Search around the natural chalcone scaffold in photoinitiating systems

Authors :
Didier Gigmes
Fabrice Morlet-Savary
Guillaume Noirbent
Hong Chen
Shaohui Liu
Damien Brunel
Jacques Lalevée
Bernadette Graff
Ke Sun
Yijun Zhang
Pu Xiao
Frédéric Dumur
Institut de Science des Matériaux de Mulhouse (IS2M)
Centre National de la Recherche Scientifique (CNRS)-Matériaux et nanosciences d'Alsace (FMNGE)
Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique
Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)
Institut de Chimie Radicalaire (ICR)
Aix Marseille Université (AMU)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Australian National University (ANU)
Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE)
Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Réseau nanophotonique et optique
Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Centre National de la Recherche Scientifique (CNRS)
ANR-17-CE08-0054,VISICAT,Nouveaux Photocatalyseurs Redox pour la Synthèse sous Lumière Visible de Réseaux Polymères Interpénétrés(2017)
Dumur, Frederic
Source :
Dyes and Pigments, Dyes and Pigments, Elsevier, 2021, 188, pp.109213. ⟨10.1016/j.dyepig.2021.109213⟩, Dyes and Pigments, 2021, 188, pp.109213. ⟨10.1016/j.dyepig.2021.109213⟩
Publication Year :
2021
Publisher :
Elsevier BV, 2021.

Abstract

Chalcones are well-known natural dyes, 18 different derivatives selected from the rational molecular design (i.e. through molecular orbital calculations) were synthesized. If used in conjunction with an amine (i.e. ethyl l, 4-(dimethylamino) benzoate, EDB) and an iodonium salt (bis(4-tert-butylphenyl) iodonium hexafluorophosphate, Iod) as photoinitiating systems (PISs), these dyes can initiate both the free radical polymerization of polyethylene glycol diacrylate (PEG-diacrylate) and the cationic polymerization of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate (EPOX) via oxidation–reduction reaction mechanisms. Furthermore, among the 18 different suggested structures, except for dyes 9 and 10, which have been synthesized and used in other fields, the remaining 16 dyes have never been synthesized before. The photopolymerization efficiency of acrylates carried out under LED@405 nm are excellent both for thin films (the thickness is about 0.2 mm) and thick films (the thickness is about 2 mm). Furthermore, all of them can also boost the cationic polymerization of EPOX upon LED irradiation at 405 nm, in the presence of an iodonium salt and an amine. More interestingly, stereoscopic 3D patterns were successfully fabricated by the direct laser write (DLW) technique which demonstrated reversible swelling properties and reversible shape-memory effects induced via swelling and dehydration for the access to 4D printing.

Details

ISSN :
01437208
Volume :
188
Database :
OpenAIRE
Journal :
Dyes and Pigments
Accession number :
edsair.doi.dedup.....d0a0ea69056dd8503927081497684c85
Full Text :
https://doi.org/10.1016/j.dyepig.2021.109213