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Publications (318)
In this work, new naphthoquinone‐based photoinitiators are synthesized and applied for the first time in free radical photopolymerization. In the presence of acrylate monomers, these PIs display excellent photoinitiation capabilities under blue‐light LED@405 nm irradiation in a two‐component photoinitiating system in which the additive is a common...
Currently, increasing attention has been focused on light-emitting diodes (LEDs)-induced photopolymerization. The common LEDs (e.g., LED at 365 nm and LED at 405 nm) possess narrow emission bands. Due to their light absorption properties, most commercial photoinitiators are sensitive to UV light and cannot be optimally activated under visible LED i...
In this study, a series of N-naphthalimide ester derivatives (noted NPIE1-NPIE9) with different substituents were designed as visible light photoinitiators (PIs). These structures exhibited good light absorption properties in the visible range. Photoinitiation abilities of NPIEs were evaluated upon exposure to a light-emitting diode at 405 nm. All...
We present a group of seven new advanced symmetric iodonium salts bearing two benzylidene-based chromophores. This is the first example of the use of a double bond in the structure of a symmetric iodonium salt. Such an improvement ensures excellent absorbing properties in the UV-A and visible range, representing a significant advance over the commo...
Novel metal oxide/polymer composite photocatalysts prepared by photocuring with common metal oxide particles (ZnO or CeO2) and acrylic ester monomers have been investigated for the first time. Metal oxide particles were fully integrated with the acrylate polymer network based on the crosslink of poly ethylene glycol diacrylate (noted below as Poly-...
In this work, a series of Type I photoinitiators (PIs) based on the naphthoquinone scaffold were designed and synthesized for the first time, in order to induce photopolymerization under visible...
The colorants found in beverages are sensitive to degradation resulting in a loss of color, which can affect the perception of the product quality by the consumer. The Fenton reaction is one of the possible degradation pathways. The Fenton oxidation process is a catalytic reaction of hydrogen peroxide (H2O2) with ferrous ions (Fe2+) that generates...
In both organic and polymer synthesis, photochemistry of Charge Transfer Complexes (CTCs) is considered as a powerful approach to expand visible‐light‐driven radical chemistry reaction. We report herein on the development of a class of useful CTCs using pyridinium salts as efficient electron acceptors (combined with N, N, 3, 5‐tetramethylaniline, T...
With the rapid development of photopolymerization, the search for new near‐UV/visible light sensitive photoinitiating system (PIS) is one of the most interesting topics in polymerization area. In this work, a new PIS (chalcone dye/amine/iodonium salt) could efficiently and simultaneously initiate the free radical photopolymerization of polyethylene...
In the past few decades, interpenetrating polymer network (IPN) hydrogels have attracted huge attention due to their special cell-like structures, interpenetrating interface, and two-phase continuity, which has special synergistic effects on their performance and function. In this work, the best candidates were selected from the firstly synthesized...
The free radical polymerization of acrylates photo‐initiated by push–pull dye‐based photoinitiating systems (PISs) is widely investigated in previous works. As a supplementary investigation on push–pull dyes, here in this article, 25 push–pull structures comprising electron acceptors derived from indane‐1,3‐dione and 1H‐cyclopenta[b]naphthalene‐1,3...
Metals Organic Frameworks (MOFs) are promising crystalline, embrittled materials generally produced in powdering form with varied remarkably functionalities. In contrary, polymers are flexible and processable materials. Therefore, obtaining shaped solids gathering polymer malleability and MOFs properties such as their photocatalytic activities, hav...
Recently, many researchers have focused their attentions on associating perovskites with polymers in order to enhance their processability and rigidity while protecting their interesting environmental properties. Therefore, this work reports the successful development of two different Perovskites/polymer composites via a simple, rapid, low-cost and...
In the last few years, pharmaceutical compounds classified as emerging pollutants have attracted the attention of many researchers, due to their massive presence in soil, surface, sewage, groundwater and drinking water, as well as to their harmful effects on human health and the environment. In this context, the degradation of four drugs with diffe...
Two water soluble oligomeric photoinitiators (OAA‐B and OAA‐BP) were synthesized by first preparing an oligo(amido amine) (OAA) via aza‐Michael addition reaction of N,N’‐methylene bisacrylamide and 1,4‐diaminobutane, then carrying out another aza‐Michael addition reaction between OAA and 4‐benzoylphenyl acrylate for OAA‐B and also diethyl vinylphos...
N-Heterocyclic carbene–borane complexes can lead to a photochemically triggered borane–acrylate click reaction, a new type of photo-click reaction. Because boranes have three substituents they can participate to cross-linking, unlike thiols in thiol–(meth)acrylate reactions. This generates materials with improved mechanical properties.
Abstract
In...
The development of 3D printing fuels the need for new photoinitiating systems working under mild conditions and/or leading to polymers with new and/or enhanced properties. In this context, we introduce herein N‐Heterocyclic Carbene‐borane complexes as reagents for a new type of photo‐click reaction, the borane‐(meth)acrylate click reaction. Remarka...
Hybrid Metal Organic-Frameworks (MOF)/polymer materials have gathered many researcher’s consideration thanks to their varied functionalities and high processability. Herein, Metal Organic Frameworks (MOFs) have been successfully incorporated into an acrylate polymer network by photopolymerization upon mild visible light irradiation at 405 nm. The s...
L−Tryptophan (L−Trp) is an amino acid important in nutrition, and mainly provided by food supplements. However, it is known to be unstable under light irradiation, which is an issue for the nutrition and feed industry. In the present study, the photostability of L−Trp was studied in acidic aqueous solutions under air and under an inert atmosphere,...
The investigation of copper-iodide cubane derivatives as new co-initiators for the free radical polymerization (FRP) of acrylate monomers under mild irradiation conditions is described for the first time here. These...
Nowadays water scarcity represents a threat for human and living beings. Therefore, to satisfy the demands of people for clean and safe water, new technologies for wastewater treatment have been developed. Thus, photocatalysis has emerged as a green chemical approach for such treatment. In this context, new polyoxometalate (POM)/polymer composites...
Silver nanoparticles (AgNPs) play a crucial role in biology and medical research as their extensive and efficient antibacterial activity and high electrical and thermal conductivity. However, the generation of them with a certain morphology under mild conditions (under air, solvent‐free, room temperature, etc.,) is still a huge challenge. Herein, a...
In this article, a series of three-component photoinitiating systems (PISs) based on push-pull dyes are proposed. The systems are composed of the newly synthesized push-pull dyes and different co-initiators, namely an iodonium salt and a tertiary amine (ethyl dimethylaminobenzoate EDB). Photoinitiation abilities and photochemical properties of the...
In this paper, seven new photoinitiators based on the benzophenone scaffold are specifically designed for photopolymerization under mild conditions upon light-emitting diodes (LEDs) irradiation i.e. four benzophenone-triphenylamine photoinitiators (noted BT1-BT4)...
In this article, the free radical polymerization of acrylates was successfully achieved with a series of twelve push-pull chromophores comprising the N-ethyl carbazole-1-allylidene group as the electron-donating group. Using this strong donor, the resulting dyes, never synthesized before, could efficiently initiate the free radical photopolymerizat...
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 photoiniti...
Four series of bis-chalcone compounds based on benzylpiperidinone, tetrahydrothiopyranone, pyridine or biphenyl central parts are designed and synthesized, enabling the development of ten bis-chalcones varying both by the central cores and by the substitution patterns (ortho, meta, para-positions) and the choice of the different groups attached to...
Redox free radical polymerization (RFRP) is considered as a cost-effective technique for the production of polymers in a very short time scale and without any energy consumption. Its principle is...
A spontaneous thiol-ene polymerization has been reported in the literature for a broad range of monomers, generally under conditions avoiding solvent, heating and the intentional formation of radicals. In the...
Herein, new iodonium salts based on 4,4-difluoro-1,3,5,7,8-pentamethyl-4-bora-3a,4a-diaza-s-indecene (B-1) chromophore has been introduced to 3D printing applications. Iodonium salts with different anions such as tosylate, hexafluorophosphate, hexafluoroantimonate, and triflate absorbing in...
Two fac-rhenium tris-carbonyl complexes bearing a pi-accepting pyridoannelated N-heterocyclic carbene (NHC) ligand with general formula Re(CO)(3) (pyipy)X, where pyipy is 2-pyridil-imidazo[1,5-a]pyridine-3-ylidene and X = CI (Re1) and Br (Re2), are investigated as photoredox catalytic systems in light-promoted polymerization reactions. Both rhenium...
Different inorganic/organic photocomposites based on polyoxometalate (POM) nanoparticles have been developed for photocatalytic applications. Currently, polyoxometalate nanoparticles have been successfully in‐situ embedded into an acrylate polymer network by photopolymerization upon mild visible light irradiation at 405 nm. The proposed POM/polymer...
Considering the synthetic relevance of heteroarenes in various areas ranging from organic synthesis to medicinal chemistry, developing practically simple methodologies to access functionalized heteroarenes is of a significant value. Described herein is an efficient approach for C–H silylation and hydroxymethylation of pyridines and related heterocy...
A series of carbazole or triphenylamine based mono-chalcones, displaying either D–π-A or A–π-D–π-A architecture, have been designed and synthesized for intense absorption bands at around 405 nm with high molar extinction coefficients around 10⁵ M⁻¹ cm⁻¹ corresponding to π–π* electronic transitions. Photosensitivity of the new photoinitiating system...
A series of eleven push–pull chromophores with specific structures have been designed
for the free radical polymerization of acrylates, but also for the fabrication of photocomposites and 3D-printed structures. New photoinitiating systems comprising the different push–pull dyes showed excellent photochemical reactivities at 405 nm. Notably, polymer...
This paper describes the development of four new coumarin chromophore-based iodonium salts as efficient one-component cationic photoinitiators upon light-emitting diode irradiations (LEDs) with maximum emission under the UV-A region at...
The design and development of high-performance photoinitiating systems applicable to visible light delivered from light-emitting diodes (LEDs) attracts an ever-increasing attention due to their great potential applications in various fields. Chalcones correspond to a well-established class of natural compounds present in many plants. In this contex...
In this article, different substituents (benzoyl, acetyl, styryl) are introduced onto the carbazole scaffold to obtain 8 novel carbazole derivatives. Interestingly, a benzoyl substituent, connected to a carbazole group, could form a benzophenone moiety, which composes a monocomponent Type II benzophenone-carbazole photoinitiator (PI). The synergeti...
This work demonstrates a new versatile, efficient photoinitiating system based on 2-amino-4-phenyl-6-(4-phenylphenyl)benzene-1,3-dicarbonitrile and 2-amino-4-phenyl-6-[4-[(E)-styryl]phenyl]benzene-1,3-dicarbonitrile derivatives as photosensitisers of iodonium and thianthrenium salts for photopolymerization under visible low light intensity with...
In this paper, we demonstrate the possibility of generating arbitrary polymer microstructures covalently linked to a first polymer layer by laser direct writing. At the molecular scale, the process relies on nitroxide-mediated photopolymerization (NMP2) triggered by a light-sensitive alkoxyamine. In addition to the proof-of-concept and examples of...
We report herein a practically simple visible-light photocatalytic approach for the synthesis of a large variety of phosphate esters through the combination of N-alkoxypyridinium salts and phosphites under mild conditions. The scope of the reaction is broad and the protocol was successfully applied to the synthesis of biologically relevant structur...
A bifunctional benzophenone-carbazole-based photoinitiator BPC was designed from its molecular structure viewpoint. To get this, two benzoyl substituents were introduced as peripheral groups of carbazole so that a molecule in which two benzophenones were fused to one carbazole unit could be obtained in a one-step procedure. As a result of this comb...
Six ketones (abbreviated as ketones 1-6) varying by the substitution pattern of the central cyclohexanones and the choice of the peripheral groups (thiophene or furane) were synthesized and proposed as unprecedented visible light sensitive photoinitiators, in combination with an amine and an iodonium salt, for the free radical polymerization of acr...
The design of photoinitiating systems with excellent photochemical reactivities at 405nm LED is one of the obstacles to efficiently promote free radical polymerization in mild conditions (e.g., low light intensity, under air). Here, our actual search for new multicomponent photoinitiating systems at 405nm LED prompts us to develop new dyes based on...
In this current contribution, we provide a detailed investigation into the photochemistry and the free radical photoinitiating reactivity of new LED light-sensitive photoinitiators (PIs). This series was designed on the basis of a judicious association of a carbazole-coumarin fused subunit and an O-acyl-α-oxooxime branch which integrates an N–O pho...
Carbazole structures are of high interest in photopolymerization due to their enhanced light absorption properties in the near-UV or even visible ranges. Therefore, type I photoinitiators combining the carbazole chromophore to the well-established phosphine-oxides were proposed and studied in this article. The aim of this article was to propose typ...
The present invention relates to compositions (self-thermally) curable on demand under the triggering action of UV-visible to near-infrared irradiation of moderate intensity, method of using same for accelerated photopolyaddition of cyclic ether-amine resins or ultrafast dark curing of cyclic ether-amine resins, and articles obtained by such method...
One of the main challenges in the field of 3D printing/vat photopolymerization is the poor adaption of existing commercial photoinitiators (PIs) for the recently popular 3D printers with the irradiation...
In a significant breakthrough from classical molecular (i.e., nonpolymeric) iodonium salts in light-induced photochemistry, the synthesis and use of new safer polymeric iodonium salts are reported here. They are shown to be involved in charge transfer complexes (CTCs) while in interaction with a safe amino acid derivative (N-phenylglycine). Also, t...
The photoinitiation abilities of three 1,2‐diketones [i.e., acenaphthenequinone (ANPQ), aceanthrenequinone (AATQ), and 9,10‐phenanthrenequinone (PANQ)]‐based photoinitiating systems [PISs, with additives such as iodonium salt, N‐vinylcarbazole (NVK), tertiary amine, and phenacyl bromide (R‐Br)] for cationic photopolymerization and free‐radical phot...
The new 2-(diethylamino)-4,6-diphenyl-benzene-1,3-dicarbonitrile derivatives were synthesized and proposed as high performance photoinitiators in conjunction with iodonium salt for: i) cationic polymerization of epoxides, ii) free-radical polymerization of acrylates, iii) the synthesis of interpenetrating polymer networks (IPNs) from acrylate/epoxy...
Mesoporous silicon (PSi) is an emerging nanomaterial studied in e.g. biomedical, sensor and energy applications. In many applications, a major obstacle in its commercial use is the instability of its surfaces, especially when functionalized with organic molecules. In the present work, we introduce a surface functionalization method for PSi, in whic...
Six novel oxime carboxylate photoinitiators were designed on the basis of a π-conjugated (E)-1-(4-styrylphenyl)-1-one subunit. Different substituent groups were introduced into three distinctive sites of the chromophore to rationalize their related electronic and structural effects on free-radical photoinitiating reactivities. The electronic proper...
Ascorbic acid is widely used in the food industry as a source of Vitamin C or as antioxidant. However, it degrades quickly in beverages at acidic pH and can accelerate the degradation of anthocyanins, natural dyes used in beverages, leading to a loss of color. In this work, we investigated the possibility to replace ascorbic acid by ascorbic acid d...
L’étude de la stabilité des colorants reste une problématique importante en chimie et un enjeu industriel. En effet, les colorants utilisés doivent être suffisamment stables dans le temps pour assurer la qualité des produits. La compréhension des mécanismes mis en jeu dans leur stabilité thermique et photochimique est ainsi indispensable. En s’appu...
Les colorants organiques sont utilisés depuis plusieurs décennies dans de nombreuses applications aussi bien dans le domaine de l’industrie que dans celui de l’art. Néanmoins, ils présentent l’inconvénient majeur d’être photosensibles. Une alternative à cet inconvénient est de créer des matériaux hybrides alliant les avantages des matrices minérale...
Photopolymerization processes, and especially those carried out under visible light, are more and more widespread for their multiple advantages compared to thermal processes. In the present paper, new 1,8-naphthalimide derivatives are proposed as photoinitiators for free-radical polymerization upon visible light exposure using light-emitting diodes...
Although N-heterocyclic carbenes (NHCs) have brought profound changes in catalytic organic synthesis, their generation generally requires inert atmosphere and harsh conditions. To overcome these limitations, an air-stable NHC photogenerator has been developed involving two mild components: 1,3‐bis(mesityl)imidazolium tetraphenylborate (IMesH+BPh4−)...
The design and development of photoinitiating systems applicable to UV or even visible light delivered from light‐emitting diodes (LEDs) has been attracting increasing attention due to their great potential applications in various fields. Compared to the strategy of synthesizing novel compounds, the exploration of existing chemicals with interestin...
New polyoxometalate (POM)/polymer hybrid composites were prepared by photopolymerization under mild conditions for suitable photocatalytic processes. Polyoxometalates were incorporated in special photosensitive resins, which were photopolymerized under visible light to obtain new materials with photocatalytic activity for dye removal. The synthesiz...
We present herein the properties of a highly reactive Type I photoinitiator with significant 2PA cross-sections (δ720nm ~ 90 GM). We demonstrate that this new type of photocleavable system exhibits...
Redox polymerizations are of huge importance throughout academic and industrial polymer science. Many authors propose the reaction of reducing (Red) and oxidizing (Ox) agents to accelerate/initiate radical or cationic polymerizations. As a result of activation energies typically below 80 kJ/mol, such reactions can occur under mild conditions, e.g.,...
In recent works, charge transfer complexes (CTCs) have proved to be useful photoinitiating agents to trigger free radical polymerization. However, because of their low molecular weights, migration issues remain very important. In line with pressing migration concerns around photoinitiating systems (e.g., in 3D polymer networks), we report here the...
Anthocyanins are natural dyes widely used in the food industry, but their chemical stability in beverages can be affected by the presence of additives. In the present paper, the interaction between anthocyanins and ascorbic acid (AA) is more particularly investigated. Ascorbic acid is an ubiquitous component in food products. In this study, the the...
In the search of smarter routes to control the conditions of N‐heterocyclic carbenes (NHCs) formation, a two‐component air‐stable NHC photogenerating system is reported. It relies on the irradiation at 365 nm of a mixture of 2‐isopropylthioxanthone (ITX) with 1,3‐bis(mesityl)imidazoli(ni)um tetraphenylborate. The photoinduced liberation of NHC is e...
This investigation presents the use of a photoredox catalyst "G1" as a photoinitiating system for free radical/ cationic hybrid polymerization under mild irradiation conditions. The G1 system (G1/iodonium salt/N-vi-nylcarbazole), can simultaneously initiate the free radical and cationic polymerization reactions upon exposure to a visible (405 nm) l...