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4 article(s) from Lalevée, Jacques

Towards new NIR dyes for free radical photopolymerization processes

Haifaa Mokbel,
Guillaume Noirbent,
Didier Gigmes,
Frédéric Dumur and
Jacques Lalevée

Beilstein J. Org. Chem. 2021, 17, 2067–2076, doi:10.3762/bjoc.17.133

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Graphical Abstract

Scheme 1: Investigated NIR dyes.

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Scheme 2: Other used chemicals.

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Scheme 3: Synthetic routes to compounds Ca, Cb, and CNa.

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Scheme 4: Synthetic routes to CI1, CI3, CI4, and CI6–CI9.

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Scheme 5: The metathesis reaction enabling the formation of “soft” salts CBPh1-CBPh4.

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Figure 1: Visible–NIR spectra of NIR dyes in ACN. A) (1) CBPh1, (2) CBPh2, (3) CBPh3, (4) CBPh4, (5) Ca, (6) ...

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Figure 2: Photopolymerization profiles of PETIA monomer under air (acrylate functions conversion vs irradiati...

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Figure 3: Photopolymerization profiles of PETIA monomer under air (acrylate functions conversion vs irradiati...

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Scheme 6: Pictures of polymers obtained for a thickness of 1.4 mm, using a NIR dye/iod/amine 0.1:3:2, %w/w/w ...

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Scheme 7: Proposed mechanism for the photochemical reactivity of NIR dyes in a three-component PIS.

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Figure 4: A) Photopolymerization profiles of PETIA/epoxy blend 1:1, w/w under air (acrylate and epoxy functio...

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Published 16 Aug 2021

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Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

Aude-Héloise Bonardi,
Frédéric Dumur,
Guillaume Noirbent,
Jacques Lalevée and
Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

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Figure 1: Typical oxidative and reductive cycle for a photoredox catalyst (PC).

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Figure 2: Transitions involved in absorbing species containing π, σ and n electrons.

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Figure 3: Ligand to metal charge transfer (illustrated here for a d⁶ metal complex).

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Figure 4: Metal to ligand charge transfer (illustrated here for a d⁵ metal complex).

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Scheme 1: Structures of additives involved in the photoredox catalytic cycles.

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Figure 5: Catalytic cycles involved with iodonium salt and (A) (TMS)₃SiH, (B) NVK and (C) EDB.

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Scheme 2: Structures of photoredox metal-based catalysts.

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Scheme 3: Photocatalytical cycle for the Ru complex.

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Scheme 4: Structures of photoredox organocatalysts.

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Scheme 5: Diversity of the chemical structures of photoredox organocatalysts.

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Scheme 6: Structures of benchmarked monomers.

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Scheme 7: Structure of the CARET additive.

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Scheme 8: Photoredox catalysis mechanism of a visible light-mediated living radical polymerization. (Abbrevia...

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Published 12 Dec 2018

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Metal and metal-free photocatalysts: mechanistic approach and application as photoinitiators of photopolymerization

Jacques Lalevée,
Sofia Telitel,
Pu Xiao,
Marc Lepeltier,
Frédéric Dumur,
Fabrice Morlet-Savary,
Didier Gigmes and
Jean-Pierre Fouassier

Beilstein J. Org. Chem. 2014, 10, 863–876, doi:10.3762/bjoc.10.83

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Scheme 1: Examples of photoinitiating systems.

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Figure 1: Previously reported PIC (based on metal complexes) [45-52].

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Figure 2: Previously reported PIC (metal free organic molecules) [54,55].

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Scheme 2: Reaction mechanisms for the three-component system PIC/eA/E-Z.

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Scheme 3: Reaction mechanisms for the two-component system PIC/eA.

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Scheme 4: Reaction mechanisms for the system PIC/eA/add.

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Scheme 5: Reaction mechanisms for the system PIC/eD/B-Y.

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Figure 3: Typical oxidation and reduction agents used through the photoredox catalysis approach in polymeriza...

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Figure 4: Typical monomers that can be polymerized through a photoredox catalysis approach.

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Scheme 6: Reaction mechanisms for the system Ru(bpy)₃²⁺/Ph₂I⁺/R₃SiH.

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Scheme 7: Reaction mechanisms for the Ru(ligand)₃²⁺/Ph₃S⁺/R₃SiH system.

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Scheme 8: Reaction mechanisms for the Ru(ligand)₃²⁺/Ph₂I⁺/NVK system upon visible lights.

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Scheme 9: Reaction mechanisms for the violanthrone/Ph₂I⁺/TTMSS (R₃SiH) system upon red lights.

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Scheme 10: Reaction mechanisms for the Tr-AD/R-Br/MDEA system upon visible lights.

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Scheme 11: The photoredox catalysis for controlled polymerization reactions.

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Scheme 12: Reaction mechanisms for the Ru(ligand)₃²⁺/MDEA/R-Br system upon visible lights.

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Scheme 13: Reaction mechanisms for the Violanthrone/Ru(ligand)₃²⁺/Ph₂I⁺/R₃SiH system upon visible lights.

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Scheme 14: Reaction mechanisms for the MK/amine/triazine system upon visible lights.

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Figure 5: The new proposed PIC (Ir(piq)₂(tmd)).

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Figure 6: UV–visible light absorption spectra for Ir(piq)₂(tmd) (2) and Ir(ppy)₃ (1); solvent: acetonitrile.

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Figure 7: (A) cyclic voltamogramm for Ir(piq)₂(tmd) in acetonitrile; (B) absorption (a) and luminescence (b) ...

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Figure 8: Photolysis of a Ir(piq)₂(tmd)/Ph₂I⁺ solution ([Ph₂I⁺] = 0.023 M, in acetonitrile) upon a halogen la...

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Figure 9: ESR spin-trapping spectra for the irradiation of a Ir(piq)₂(tmd)/Ph₂I⁺ solution in the presence of ...

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Figure 10: (A) Photopolymerization profile of EPOX; photoinitiating system: Ir(piq)₂(tmd)/Ph₂I⁺/NVK (1%/2%/3%)...

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Figure 11: (A) Photopolymerization profile of TMPTA; initiating systems: (1) Ir(piq)₂(tmd)/MDEA (1%/2%) and (2...

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Published 15 Apr 2014

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New core-pyrene π structure organophotocatalysts usable as highly efficient photoinitiators

Sofia Telitel,
Frédéric Dumur,
Thomas Faury,
Bernadette Graff,
Mohamad-Ali Tehfe,
Didier Gigmes,
Jean-Pierre Fouassier and
Jacques Lalevée

Beilstein J. Org. Chem. 2013, 9, 877–890, doi:10.3762/bjoc.9.101

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Scheme 1: Typical reactions for photoinitiated cationic polymerization.

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Scheme 2: Examples of previously investigated architectures.

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Scheme 3: Investigated Co_Pys.

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Scheme 4: Other chemical compounds.

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Figure 1: UV–vis absorption spectra of the investigated compounds: (A) In acetonitrile for Py_1 and acetonitr...

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Figure 2: HOMO–LUMO orbitals for Py_2, Py_3, Py_5, Py_6, Py_8, Py_11 and Py_12 involved in the π–π* transitio...

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Figure 3: Fluorescence quenching of ¹Py_3 by the phenacylbromide (PBr) in acetonitrile/toluene (50/50). Inser...

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Scheme 5: Photochemical processes for the different Co_Pys.

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Figure 4: ESR spectra obtained upon irradiation of (A) Py_3/Iod, (B) Py_3/PBr and (C) Py_3/EDB in tert-butylb...

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Figure 5: ESR-spin trapping spectra of Py_9/Iod in tert-butylbenzene (storage at rt for 24 h); (a) experiment...

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Figure 6: Photopolymerization profiles of EPOX upon Xe–Hg lamp irradiation (λ > 340 nm) under air for differe...

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Figure 7: Photopolymerization profiles of EPOX upon a Xe–Hg lamp irradiation (λ > 340 nm) under air for diffe...

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Figure 8: (A) Photopolymerization profiles of EPOX-Si upon a Xe–Hg lamp irradiation (λ > 340 nm) under air fo...

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Figure 9: Photopolymerization profiles of TMPTA upon Xe–Hg lamp irradiation (λ > 340 nm) in laminate for diff...

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Figure 10: Photolysis of (A) the Py_3/PBr couple, (B) the Py_3/Iod couple, and (C) the Py_3/MDEA couple; Xe–Hg...

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Figure 11: Photolysis of (A) the Py_11/Iod and (B) the Py_11/Iod/NVK couple. Halogen lamp irradiation. In acet...

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Scheme 6: The oxidative cycle.

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Scheme 7: Oxidation versus reduction cycles.

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Published 07 May 2013

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