Photochemistry and Radical Chemistry under Low  Intensity Visible Light Sources: Application to Photopolymerization Reactions

Lalevée, Jacques; Morlet‐Savary, Fabrice; Dietlin, Céline; Graff, Bernadette; Fouassier, Jean‐Pierre

doi:10.3390/molecules190915026

Cited by 18 publications

(13 citation statements)

References 51 publications

(130 reference statements)

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“…As such, the concentration of PC •+ /Br − is decreased under lower irradiation, as this complex is generated through activation. 36 Herein, the influence of light intensity and PC concentration are investigated as factors that affect the performance of OATRP by its modulation of [ 3 PC*], using PCs 1 and 2 as catalysts for the polymerization of methyl methacrylate (MMA).…”

Section: Introductionmentioning

confidence: 99%

Impact of Light Intensity on Control in Photoinduced Organocatalyzed Atom Transfer Radical Polymerization

et al. 2017

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Organic photoredox catalysts have been shown to operate organocatalyzed atom transfer radical polymerizations (O-ATRP) using visible light as the driving force. In this work, the effect of light intensity from white LEDs was evaluated as an influential factor in control over the polymerization and the production of well-defined polymers. We posit the irradiation conditions control the concentrations of various catalyst states necessary to mediate a controlled radical polymerization. Systematic dimming of white LEDs allowed for consideration of the role of light intensity on the polymerization performance. The general effects of decreased irradiation intensity in photoinduced O-ATRP were investigated through comparing two different organic photoredox catalysts: perylene and an 3,7-di(4-biphenyl) 1-naphthalene-10-phenoxazine. Previous computational efforts have investigated catalyst photophysical and electrochemical characteristics, but the broad and complex effects of varied irradiation intensity as an experimental variable on the mechanism of O-ATRP have not been explored. This work revealed that perylene requires more stringent irradiation conditions to achieve controlled polymer molecular weight growth and produce polymers with dispersities <1.50. In contrast, the 3,7-di(4-biphenyl) 1-naphthalene-10-phenoxazine is more robust, achieving linear polymer molecular weight growth under relative irradiation intensity as low as 25%, to produce polymers with dispersities <1.50. This finding is significant, as the discovery of highly robust catalysts is necessary to allow for the adoption of successful O-ATRP in a wide scope of conditions, including those which necessitate low light intensity irradiation.

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Section: Introductionmentioning

confidence: 99%

Impact of Light Intensity on Control in Photoinduced Organocatalyzed Atom Transfer Radical Polymerization

et al. 2017

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“…And these attempts include the following aspects. Light harvesting PI or PIS with excellent photoinitiator efficiencies are developed by using a suitable skeleton decorated with cleavable type I PI units or photosensitizer units of type II PIS; Photoredox catalysis from the metal complexes is used as efficient photosensitizers for the photopolymerization upon soft irradiation conditions and even in the air; One‐component PIs are synthesized by chemically incorporating the co‐initiator moiety into the photosensitizer chromophores . In this case, the initiator efficiency is enhanced and simultaneously the odor, toxicity, and migration problems from amine hydrogen donors are overcome. Novel PISs based on three‐component systems are designed to dramatically enhance the photoinitiator efficiency.…”

Section: Introductionmentioning

confidence: 99%

“…In this case, the initiator efficiency is enhanced and simultaneously the odor, toxicity, and migration problems from amine hydrogen donors are overcome. Novel PISs based on three‐component systems are designed to dramatically enhance the photoinitiator efficiency. And the oxygen inhibition effect can be expected to be counterbalanced by this strategy . The involved three‐component PISs are based on the different combinations of a light absorbing compound, amine, mercapto‐compound, onium salt, triazine derivatives, maleimide, or maleic anhydride, bromocompound, etc .…”

Section: Introductionmentioning

confidence: 99%

High performance of the linked visible photoinitiator for free radical polymerization based on erythrosine B derivative

Nan

Huang

Fan

et al. 2015

J of Applied Polymer Sci

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A novel erythrosine B derivative linked with a tertiary amine used as a visible light initiator for free radical polymerization was synthesized and characterized. For comparison, the free hydrophobic erythrosine B derivative was also synthesized and its combination with the tertiary amine was used as the separated two component photoinitiator. The linked initiator exhibited higher photoinitiator efficiency in high viscosity monomer than in low viscosity one, compared with the separated counterpart. Especially, when it was combined with iodonium salt, the further promotion of the photoinitiator efficiency was observed, compared with the separated three component system. It was found that as iodonium salt together with tertiary amine was continuously added to the formula with the linked initiator, the photoinitiator efficiency was dramatically enhanced compared with the same addition to the formula with the separated counterpart, revealing the application potential of the linked initiator. And the continuous addition of either the iodium salt or the tertiary amine to the formula only leaded to the small size increase of the photoinitiator efficiency. These results suggested that there existed an interdependent relationship between iodonium salt and tertiary amine in promoting the photoinitiator efficiency of the dye/amine/iodonium salt system. For these, the corresponding synergistic mechanism was proposed.

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“…In FRP and FRPCP, oxygen inhibition is a serious drawback that does not exist in CP but the use of high intensity irradiation devices (a few W cm ‐2 ) allows to overcome this detrimental effect . Under exposure to low intensity sources (a few mW cm –2 ), FRP becomes rather hard in contrast to CP . Suitable PISs being able to overcome the oxygen inhibition still ensure excellent polymerization profiles in FRPCP .…”

Section: Introductionmentioning

confidence: 99%

“…ref. [1k],, and the particular use of the LED technology outlined in a recent review . In CP and FRPCP, two‐ and three‐component PISs are currently used (see below).…”

Section: Introductionmentioning

confidence: 99%

Cationic Photoinitiators for Near UV and Visible LEDs: A Particular Insight into One‐Component Systems

Zhang

Xiao

Dietlin

et al. 2016

Macro Chemistry & Physics

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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 Emitting Diodes (LEDs). In this review, a special emphasis is provided on the most recent and promising cationic initiators operating under near UV and visible LEDs. Ferrocenium salts exhibit the broadest visible light absorption and are probably, from this point of view, the most versatile near UV and visible light cationic initiators. Excellent photoinitiation performance has been found with the ferrocenium salts as one‐component initiators, and the effect of ferrocenium salts based multi‐component photoinitiating systems on the relevant photoinitiation performance has also been investigated.

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Photochemistry and Radical Chemistry under Low Intensity Visible Light Sources: Application to Photopolymerization Reactions

Cited by 18 publications

References 51 publications

Impact of Light Intensity on Control in Photoinduced Organocatalyzed Atom Transfer Radical Polymerization

Impact of Light Intensity on Control in Photoinduced Organocatalyzed Atom Transfer Radical Polymerization

High performance of the linked visible photoinitiator for free radical polymerization based on erythrosine B derivative

Cationic Photoinitiators for Near UV and Visible LEDs: A Particular Insight into One‐Component Systems

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