Céline Dietlin's research while affiliated with Université de Haute-Alsace and other places
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Publications (108)
In this work, eleven heteroleptic copper complexes were designed and studied as photoinitiators of polymerization in three-component photoinitiating systems in combination with an iodonium salt and an amine. Notably, ten of them exhibited panchromatic behavior and could be used for long wavelengths. Ferrocene-free copper complexes were capable of e...
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...
Two new copper complexes were investigated in three-component visible light photoinitiating system for both radical and cationic polymerisation under air. Their reactivity and efficiency have been compared with that of a highly efficient photoredox catalyst. The formation of acrylate/epoxy interpenetrated polymer networks were successfully performe...
Three thioxanthone derivatives differing by their peripheral groups have been investigated as visible light photoinitiators of polymerisation. Their reactivity and efficiency have been compared with that of a commercial type II photoinitiator (2-isopropylthioxanthone – ITX) in the case of free radical polymerisation, cationic polymerisation and int...
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...
Free radical polymerization is often performed by thermal initiation but also more and more by light-assisted polymerization processes. This second approach allows the polymerization to be carried out under mild conditions (under air, upon blue light exposure, under low light intensity). The aim and the originality of the present paper is to perfor...
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...
Nowadays photo semiconductors such as ZnO are one of the driving forces of humanity towards economically and ecological safe life. Such semiconductors are used in solar applications and for light emission but also multiple investigations using the material as photocatalysts (water‐splitting), or as photo initiators were published. The combination o...
Polymerization of (meth)acrylate resins upon near‐infrared (NIR) light remains a huge challenge. In this study, a new photoinduced method of polymerization of methacrylic monomers is presented, originally merging a photochemical and a photothermal pathway. A four‐component system is proposed comprising an NIR dye combined with an iodonium salt, a p...
Polydiacetylene (PDA) materials are appealing and gaining increasing research interest due to their outstanding chromatic transition and fluorescence enhancement effects upon exposure to various environmental stimuli. However, despite the photomask method, there are very few reports about the spatial controllable photopolymerization and subsequent...
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...
Superhydrophobic surfaces with a water contact angle greater than 150° were prepared by one-step photoinduced crosslinking of a tetraethyl-orthosilicate and a fluorinated organosilane mixture using an efficient photobase catalytic system. Infrared spectroscopy and electron microscopy techniques enabled to investigate the alkoxysilane condensation a...
In this article, near-infrared dyes of different structures have been investigated as new photoinitiators/photosensitizers for the free radical polymerization (FRP) of methacrylates upon Near Infrared (NIR) light exposure using Laser Diode @785 nm, @940 nm and @1064 nm. Interestingly, the use of squaraine, squarylium, boron-pyrromethene and porphyr...
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...
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...
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...
Ferrocene-based photoredox catalysis is proposed here for the first time. Aryl radicals generated from a Fe(II)*/Ar2I+ reaction can be used as initiating species for efficient free radical photopolymerization of methacrylate resins. Remarkably, these photoredox catalysts can also be used for redox free radical polymerization (without light) in comb...
A new generation of light-induced production of polymeric materials is presented here. In detail, we propose to use photoacidic catalysis during the well-known epoxy-amine polyaddition reaction: it is now referred to as "epoxy-amine photopolyaddition". Soft irradiation (405 nm visible light, 150-450 mW/cm2) of a photosensitizer/iodonium salt system...
N-Heterocyclic carbene-boranes (NHC-boranes, NHCBs) were recently described as efficient coinitiators for the visible light photopolymerization of hydroxyethyl methacrylate (HEMA) in the presence of water. In this work, a new, more water-soluble, NHC-borane - 2,4-dimethyl-1,2,4,5-tetrazol-3-ylidene borane - has been synthesized, and its efficiency...
Highly versatile initiating systems for thermal, redox, and photopolymerization processes are proposed. The photopolymerization using the multifunctional amine tris[4-(diethylamino)phenyl]amine (t4epa) and iodonium salt (Iod) as photoinitiating system (PIS) is presented. Methacrylate function conversion up to 84% was reached under [email protected]...
The combination of thermally induced and photoinduced free radical polymerization of (meth)acrylic monomers has only been scarcely presented in the literature. In this study, a two-component system with a near-infrared (NIR) dye combined with a thermal initiator is presented. The dye acts as a very efficient heat generator (heater) upon irradiation...
Photoredox catalysis based on the [Cu(neo)(DPEphos)]BF4 copper complex allowed getting a significant improvement of the polymerization performances (e.g., thick samples, coatings...) compared to that obtained with other benchmarked photoinitiators in both cationic (CP) and free radical polymerizations (FRP). Nevertheless, as for other copper comple...
A novel strategy for the preparation of extremely thick composites by photochemical and/or thermal free radical polymerization (FRP) and/or cationic polymerization (CP) under low-energy consumption visible light emitted diodes (LEDs) is described. The approach is based on the use of charge transfer complexes (CTCs) formed between N-aromatic amines...
New peroxide-free, amine-free, and phosphine-free redox free radical polymerization (RFRP) initiating systems comprising remarkably stable (i) metal acetylacetonates (Mn(acac)3, Cu(acac)2) and (ii) carbonyl compounds bearing labile hydrogen in the α-position are presented for polymerization initiation under mild conditions (under air, at room tempe...
Redox free-radical polymerizations have widespread applications but still clearly suffer from poor time control of the reaction. Currently, the workability (delay of the gel time) in redox polymerization after mixing is possible thanks to two main types of inhibitors (radical scavengers): phenols and nitroxides. Out of this trend, we propose in thi...
Disclosed herein is a dental composition having a polymerization initiator system with an aromatic tertiary phosphine compound. Further disclosed is the use of the aromatic tertiary phospine compound for the preparation of a photocurable dental compositions.
Free radical polymerization (FRP) initiation from metal acetylacetonate–bidentate ligand interaction (MABLI) under mild conditions (room temperature, under air) is discussed here for different metal centers (Mn, V, and Cu). First, without light, in MABLI systems such as V(acac)3/2-diphenylphosphinobenzoic acid (2dppba), Mn(acac)3/2dppba, or Cu(acac...
The use of new stable copper acetylacetonates in combination with specific bidentate ligands (e.g 2dppba) is proposed for redox free radical polymerization (FRP) under mild conditions (under air, room temperature). These systems show high performances competitive with reference redox initiating systems (amine/benzoylperoxide). Remarkably, some of t...
A novel photoinitiating system uses a copper photoredox catalyst (G1) in combination with an iodonium salt and N-vinylcarbazole. This provided very efficient cationic polymerisation when using LEDs or a halogen lamp. As G1 is a catalyst, it can be effective at very low concentrations. I n the polymer industry, the photopolymeri-sation process is co...
A novel photoinitiating system uses a copper photoredox catalyst (G1) in combination with an iodonium salt and N-vinylcarbazole. This provided very efficient cationic polymerisation when using LEDs or a halogen lamp. As G1 is a catalyst, it can be effective at very low concentrations. I n the polymer industry, the photopolymeri-sation process is co...
Metal Acetylacetonates – Bidentate Ligand Interaction (MABLI) is presented here as a new chemical mechanism for highly efficient generations of free radicals for polymer synthesis. This MABLI process involves simultaneous ligand exchange and change of metal oxidation degree and is associated with the efficient release of free radicals. In conventio...
The ever increasing applications of photopolymers from historical thin (<50 µm) coatings to very deep samples (>1 cm) require the development of robust 4D monitoring strategies able to assess photopolymerization efficiencies (first dimension) as a function of time (second dimension) and position (third and fourth dimensions). Therefore, here, we de...
Simultaneous redox free radical polymerization (FRP) and redox cationic polymerization (CP) are combined for the synthesis of methacrylate/diepoxide interpenetrating polymer networks (IPN). At first, the Cu(acac)2/phosphine/iodonium salt operates according to the principles of free radical promoted cationic polymerization (FRPCP). A photoactivation...
Photoinitiators exhibiting an efficient thermally activated delayed fluorescence (TADF) are investigated. Known TADF metal complexes (copper-based structures) and purely organic molecules (carbazole/sulfone based organic structures) are used, for the first time, in the FRP of methacrylates, the CP of diepoxides and the synthesis of acrylate/diepoxi...
Charge transfer complexes (CTC) between N-aromatic amines (donors) and iodonium salts (acceptors) are used here as photoinitiating systems (PIS) for the polymerization of clear methacrylate formulations under a 405 nm LED irradiation. Outstandingly, a complete spatial and temporal resolution is kept for 50 μm resolved 3D printed photopolymers at 40...
The photopolymerization processes are currently associated with thin samples for which the light penetration is good enough to activate the photoinitiator or the photoinitiating system for the entre sample’s thickness. The photopolymerization of very thick films and in shadow areas where the light penetration is inhibited (e.g in filled, pigmented,...
Dental composition comprising
(a) a homogeneous phase comprising monomer combinations (i) and (ii), (i) and (iii), (ii) and (iii), or (i), (ii) and (iii), or
comprising monomer (iii), wherein
(i) represents one or more compounds having one or more radically polymerizable carbon-carbon double bonds;
(ii) represents one or more compounds having one o...
Silyl glyoxylates are proposed here as a new class of high performance type I photoinitiators for free radical polymerization under air or in laminate (e.g., (meth)acrylates) upon exposure to different near-UV (at 395 nm; at 405 nm) and blue (at 477 nm) LEDs. The new proposed photoinitiators can also be used in the presence of additives that can en...
The first use of a new mechanosynthesized copper complex (Cu(acac)(2dppba)) as a initiator for the redox and redox photoactivated polymerization of methacrylates under air is proposed. This paper (i) describes the mechanosynthesis of this complex, (ii) outlines the relative efficiency of the complex for redox polymerization (mechanosynthesized prod...
The goal of this paper concerns the development of photoinitiating systems usable in industrial processes for coating applications (cationic polymerization of epoxide based resins), the manufacture of Interpenetrating Polymer Networks (IPNs) (polymerization of acrylate/epoxy blend) and the production of thick epoxy/glass fibres composites. For thes...
Novel copper complex based initiating systems for redox free radical polymerization (FRP) of methacrylate resins under mild conditions are proposed. Remarkably, the FRP performance of the Cu(I)/Ascorbic Acid (Vitamin C - VitC)/ benzoyl peroxide (BPO) redox system is noticeably more active than that of the amine/BPO reference especially at the top s...
The free radical polymerization of low viscosity methacrylate blends upon a LED irradiation at 405 nm under air is carried out using Cu(I)/iodonium salt/tin(II) organic derivative as photoinitiating systems. The system exhibits a high reactivity; where tin derivative plays a crucial role. It operates through a catalytic cycle in which Cu(I) is rege...
![Examples DKSi [mol-%] EDB [mol-%] DPI [mol-%] Δ R H [kJ/mol] t hmax [min]](profile/Joachim-Klee/publication/316477637/figure/tbl4/AS:954171746439174@1604503680996/Examples-DKSi-mol-EDB-mol-DPI-mol-D-R-H-kJ-mol-t-hmax-min_Q320.jpg)
The present invention relates to a dental composition comprising a specific polymerization initiator system comprising a compound having an acylsilyl- or acylgermanyl-group. The present invention also relates the use of the compound having an acylsilyl- or acylgermanyl-group for the preparation of a dental composition.
A novel way to counterbalance the drawbacks and advantages of photopolymerization and redox polymerization is proposed. Photoinitiating systems based on charge transfer complexes (CTC) between a phosphine and an iodonium salt as well as an amine and iodonium salt are checked for the free radical polymerization of methacrylates. Polymer materials as...
A strong drawback of the photoinitiators of cationic polymerization or photoacids is the photosensitivity for short and energetic wavelengths preventing their general use (specialized photochemical equipment with safety concerns must be used). In the present paper, a novel iodonium salt bearing a naphthalimide moiety (naphthalimide-Ph-I⁺-Ph) is pro...
Tue present invention relates to a dental composition comprising a polymerization initiator system comprising an aromatic tertiary phosphine compound, as well as to a use of said aromatic tertiary phosphine compound for the preparation of a photo - curable dental composition.
Efficient redox initiating systems for radical polymerizations under air usually show some severe drawbacks such as handling and toxicity of the oxidizing agent (peroxides, persulfates, peroxidiphosphates, disulfides, etc.), toxicity of the reducing agent (aromatic amines such as 4-N,N-trimethylaniline), and more generally a low top surface convers...
The objectives of this work is to propose a novel low migration additive (i.e. a phosphine) to overcome the oxygen inhibition in camphorquinone CQ base photoinitiating system for the polymerization of methacrylates (e.g. a bisphenol A-glycidyl methacrylate (Bis-GMA)/triethyleneglycol dimethacrylate (TEGDMA) blend (70%/30% w/w)) upon exposure to a c...
Objectives:
The aim of our study is to find an amine free photoinitiating system (PIS) for the polymerization of representative dental methacrylate resins. A photoinitiating system (PIS) based on camphorquinone (CQ)/triphenylgermanium hydride/diphenyl iodonium hexafluorophosphate is proposed and compared to the conventional CQ/amine couple. The po...
In the present paper, new photoinitiators based on the meta-terphenyl scaffold in combination with an iodonium salt and 9H-carbazole-9-ethanol (CARET) are proposed for the free radical promoted cationic polymerization of epoxides upon visible light exposure using light emitting diodes at 405, 455, and 470 nm. Remarkably, a new high performance addi...
The observed development of one-component photoinitiators of cationic polymerization reactions in the last forty years is briefly described. Cationic photoinitiators can usually be activated by short wavelengths (<300 nm) and relatively hard conditions (high intensity). The search for cheaper and safer light sources has led to the use of Light Emit...
A series of naphthalimide derivatives containing tertiary amine groups (DNNDs) have been prepared. Some of these derivatives (e.g. DNND3, DNND4 and DNND5) exhibit interesting shifted absorption so that they can be utilized as versatile photoinitiators upon exposure to various violet and blue LEDs (385, 405, 455 and 470 nm). They are particularly ef...
As with all nanomaterials, characterization of the surface chemistry of mesoporous silicon (PSi) is crucial for the development in its diverse applications. Nuclear magnetic resonance (NMR) is one of the most powerful methods to study the chemistry of nanomaterials, but it is currently underutilized with PSi due to low signal-to-noise ratios achiev...
The LED technology knows a fast development that holds great promise. Advanced capabilities, operating economics and environmental advantages are the main driving factors. Therefore, this paper is focused on i) the recent development of the LED technology allowing the design of novel and efficient light sources for the free radical and cationic pho...
Recently, long n-alkyltrimethoxysilanes (H3C(CH2)nSi(OCH3)3) have proven to self-assemble into mesoscopically ordered passive lamellar films through an efficient solvent-free photoacid-catalysed sol–gel process. By using an analogue precursor architecture presenting a terminal ester group (H3COC(O)(CH2)10Si(OCH3)3), both functional and tuneable nan...
N,N'-dibutylquinacridone (DBQA) is utilized here for the first time as a high-performance panchromatic photoinitiator for the cationic polymerization (CP) of epoxides, the free radical polymerization (FRP) of acrylates, the thiol-ene polymerization and the synthesis of interpenetrated polymer networks (epoxide/acrylate) under violet, blue, green an...
The search for radical initiators able to work under soft conditions is a great challenge, driven by the fact that the use of safe and cheap light sources is very attractive. In the present paper, a review of some recently reported photoinitiating systems for polymerization under soft conditions is provided. Different approaches based on multi-comp...
While the photopatterning of self-assembled monolayers (SAMs) has been extensively investigated, much less attention has been given to highly ordered multilayer systems. By being both thicker (0.5 - 2 µm) and more stable (cross-linked) than SAMs, patterned hybrid multilayers lend themselves more easily to development of technology relevant material...
The oxygen inhibition of acrylate photopolymerization using visible light was depth characterized by confocal Raman microscopy. The sample thickness was found to influence the depth conversion profile. With increasing sample thickness, the conversion at the surface was increased and the oxygen-affected layer (OAL) decreased, up to a limit where the...
While a hexahistidine affinity tag can be introduced at protein termini or internal sites by standard molecular biology procedures for purification, immobilization, or labeling of proteins, here the versatility of this concept is exploited for the chemical preparation of novel hexahistidine-tagged single-walled carbon nanotubes (His6-tagSWNTs), a n...