Naphthyl-Naphthalimides as High-Performance Visible Light Photoinitiators for 3D Printing and Photocomposites Synthesis

Mahmoud  Rahal; Bernadette  Graff; Joumana  Toufaily; Tayssir Hamieh; Malika  Ibrahim-Ouali; Frédéric Dumur; Jacques Lalevée

doi:10.3390/catal11111269

Naphthyl-Naphthalimides as High-Performance Visible Light Photoinitiators for 3D Printing and Photocomposites Synthesis

Mahmoud Rahal, Bernadette Graff, Joumana Toufaily, Tayssir Hamieh, Malika Ibrahim-Ouali, Frédéric Dumur^*, Jacques Lalevée^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

In this article, five new organic dyes based on the naphthalimide scaffold (Napht-1–Napht-5) were synthesized and tested as high-performance photoinitiators for both the Free Radical Photopolymerization (FRP) of acrylates and the Cationic Polymerization (CP) of epoxides using blue Light-Emitting Diodes (LEDs) as a safe irradiation source (LED @405 nm and 455). In fact, very good photopolymerization profiles (high final conversions and high polymerization rates) were obtained once these photoinitiators were combined with an Iodonium salt (Iod) or Iod/amine NPG and NVK). Remarkably, these dyes were able to generate interpenetrating polymer networks (IPN) by polymerization of a blend of monomers. These experiments were carried out to improve the polymerization profiles as well as the mechanical properties of the obtained materials. Due to their
high photoinitiation abilities, these compounds were used in some applications such as photocomposite synthesis, direct laser write, and 3D printing experiments. To determine the chemical mechanisms, the photochemical/photophysical properties of these compounds were studied using different characterization techniques such as UV–visible absorption spectroscopy, steady-state photolysis, Fluorescence quenching, time-resolved fluorescence spectroscopy, FTIR spectroscopy, and cyclic voltammetry.

Original language	English
Article number	1269
Pages (from-to)	1269-1285
Number of pages	16
Journal	Catalysts
Volume	11
Issue number	11
DOIs	https://doi.org/10.3390/catal11111269
Publication status	Published - Nov 2021

Keywords

3D printing
ANHYDRIDE DERIVATIVES
DESIGN
LED
LED; 3D printing
LEDS
PHOTOCATALYSTS
POLYMERIZATION REACTIONS
RADICAL PHOTOPOLYMERIZATIONS
SYSTEMS
cationic polymerization
free radical polymerization
naphthalimide
photocomposites

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@article{6e17a94bd0184e669af325f978ff4834,

title = "Naphthyl-Naphthalimides as High-Performance Visible Light Photoinitiators for 3D Printing and Photocomposites Synthesis",

abstract = "In this article, five new organic dyes based on the naphthalimide scaffold (Napht-1–Napht-5) were synthesized and tested as high-performance photoinitiators for both the Free Radical Photopolymerization (FRP) of acrylates and the Cationic Polymerization (CP) of epoxides using blue Light-Emitting Diodes (LEDs) as a safe irradiation source (LED @405 nm and 455). In fact, very good photopolymerization profiles (high final conversions and high polymerization rates) were obtained once these photoinitiators were combined with an Iodonium salt (Iod) or Iod/amine NPG and NVK). Remarkably, these dyes were able to generate interpenetrating polymer networks (IPN) by polymerization of a blend of monomers. These experiments were carried out to improve the polymerization profiles as well as the mechanical properties of the obtained materials. Due to theirhigh photoinitiation abilities, these compounds were used in some applications such as photocomposite synthesis, direct laser write, and 3D printing experiments. To determine the chemical mechanisms, the photochemical/photophysical properties of these compounds were studied using different characterization techniques such as UV–visible absorption spectroscopy, steady-state photolysis, Fluorescence quenching, time-resolved fluorescence spectroscopy, FTIR spectroscopy, and cyclic voltammetry.",

keywords = "3D printing, ANHYDRIDE DERIVATIVES, DESIGN, LED, LED; 3D printing, LEDS, PHOTOCATALYSTS, POLYMERIZATION REACTIONS, RADICAL PHOTOPOLYMERIZATIONS, SYSTEMS, cationic polymerization, free radical polymerization, naphthalimide, photocomposites",

author = "Mahmoud Rahal and Bernadette Graff and Joumana Toufaily and Tayssir Hamieh and Malika Ibrahim-Ouali and Fr{\'e}d{\'e}ric Dumur and Jacques Lalev{\'e}e",

note = "Funding Information: Funding: This research was funded by The Association of Specialization and Scientific Guidance, the Centre National de la Recherche Scientifique, Aix Marseille Universit{\'e} and the Universit{\'e} de Haute Alsace. This research was also funded by the Agence Nationale de la Recherche (ANR agency) through the PhD grant of Guillaume Noirbent (ANR-17-CE08-0054 VISICAT project). Funding Information: This research was funded by The Association of Specialization and Scientific Guidance, the Centre National de la Recherche Scientifique, Aix Marseille Universit? and the Universit? de Haute Alsace. This research was also funded by the Agence Nationale de la Recherche (ANR agency) through the PhD grant of Guillaume Noirbent (ANR-17-CE08-0054 VISICAT project). Funding Information: Acknowledgments: The Lebanese group would like to thank “The Association of Specialization and Scientific Guidance” (Beirut, Lebanon) for funding and supporting this scientific work. Aix Marseille University and the Centre National de la Recherche Scientifique (CNRS) are acknowledged for financial support. Publisher Copyright: {\textcopyright} 2021 by the author. Licensee MDPI, Basel, Switzerland.",

year = "2021",

month = nov,

doi = "10.3390/catal11111269",

language = "English",

volume = "11",

pages = "1269--1285",

journal = "Catalysts",

issn = "2073-4344",

publisher = "Multidisciplinary Digital Publishing Institute (MDPI)",

number = "11",

}

TY - JOUR

T1 - Naphthyl-Naphthalimides as High-Performance Visible Light Photoinitiators for 3D Printing and Photocomposites Synthesis

AU - Rahal, Mahmoud

AU - Graff, Bernadette

AU - Toufaily, Joumana

AU - Hamieh, Tayssir

AU - Ibrahim-Ouali, Malika

AU - Dumur, Frédéric

AU - Lalevée, Jacques

N1 - Funding Information: Funding: This research was funded by The Association of Specialization and Scientific Guidance, the Centre National de la Recherche Scientifique, Aix Marseille Université and the Université de Haute Alsace. This research was also funded by the Agence Nationale de la Recherche (ANR agency) through the PhD grant of Guillaume Noirbent (ANR-17-CE08-0054 VISICAT project). Funding Information: This research was funded by The Association of Specialization and Scientific Guidance, the Centre National de la Recherche Scientifique, Aix Marseille Universit? and the Universit? de Haute Alsace. This research was also funded by the Agence Nationale de la Recherche (ANR agency) through the PhD grant of Guillaume Noirbent (ANR-17-CE08-0054 VISICAT project). Funding Information: Acknowledgments: The Lebanese group would like to thank “The Association of Specialization and Scientific Guidance” (Beirut, Lebanon) for funding and supporting this scientific work. Aix Marseille University and the Centre National de la Recherche Scientifique (CNRS) are acknowledged for financial support. Publisher Copyright: © 2021 by the author. Licensee MDPI, Basel, Switzerland.

PY - 2021/11

Y1 - 2021/11

N2 - In this article, five new organic dyes based on the naphthalimide scaffold (Napht-1–Napht-5) were synthesized and tested as high-performance photoinitiators for both the Free Radical Photopolymerization (FRP) of acrylates and the Cationic Polymerization (CP) of epoxides using blue Light-Emitting Diodes (LEDs) as a safe irradiation source (LED @405 nm and 455). In fact, very good photopolymerization profiles (high final conversions and high polymerization rates) were obtained once these photoinitiators were combined with an Iodonium salt (Iod) or Iod/amine NPG and NVK). Remarkably, these dyes were able to generate interpenetrating polymer networks (IPN) by polymerization of a blend of monomers. These experiments were carried out to improve the polymerization profiles as well as the mechanical properties of the obtained materials. Due to theirhigh photoinitiation abilities, these compounds were used in some applications such as photocomposite synthesis, direct laser write, and 3D printing experiments. To determine the chemical mechanisms, the photochemical/photophysical properties of these compounds were studied using different characterization techniques such as UV–visible absorption spectroscopy, steady-state photolysis, Fluorescence quenching, time-resolved fluorescence spectroscopy, FTIR spectroscopy, and cyclic voltammetry.

AB - In this article, five new organic dyes based on the naphthalimide scaffold (Napht-1–Napht-5) were synthesized and tested as high-performance photoinitiators for both the Free Radical Photopolymerization (FRP) of acrylates and the Cationic Polymerization (CP) of epoxides using blue Light-Emitting Diodes (LEDs) as a safe irradiation source (LED @405 nm and 455). In fact, very good photopolymerization profiles (high final conversions and high polymerization rates) were obtained once these photoinitiators were combined with an Iodonium salt (Iod) or Iod/amine NPG and NVK). Remarkably, these dyes were able to generate interpenetrating polymer networks (IPN) by polymerization of a blend of monomers. These experiments were carried out to improve the polymerization profiles as well as the mechanical properties of the obtained materials. Due to theirhigh photoinitiation abilities, these compounds were used in some applications such as photocomposite synthesis, direct laser write, and 3D printing experiments. To determine the chemical mechanisms, the photochemical/photophysical properties of these compounds were studied using different characterization techniques such as UV–visible absorption spectroscopy, steady-state photolysis, Fluorescence quenching, time-resolved fluorescence spectroscopy, FTIR spectroscopy, and cyclic voltammetry.

KW - 3D printing

KW - ANHYDRIDE DERIVATIVES

KW - DESIGN

KW - LED

KW - LED; 3D printing

KW - LEDS

KW - PHOTOCATALYSTS

KW - POLYMERIZATION REACTIONS

KW - RADICAL PHOTOPOLYMERIZATIONS

KW - SYSTEMS

KW - cationic polymerization

KW - free radical polymerization

KW - naphthalimide

KW - photocomposites

U2 - 10.3390/catal11111269

DO - 10.3390/catal11111269

M3 - Article

SN - 2073-4344

VL - 11

SP - 1269

EP - 1285

JO - Catalysts

JF - Catalysts

IS - 11

M1 - 1269

ER -