Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Zhang, Houcheng; Zivic, Nicolas; Dumur, Frédéric; Xiao, Pu; Graff, Bernadette; Fouassier, Jean Pierre; Gigmès, Didier; Lalevée, Jacques

doi:10.1002/cptc.201800006

Cited by 47 publications

(29 citation statements)

References 46 publications

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“…Over the years, a wide range of families have been designed and synthesized as efficient photoinitiators of polymerization, activable under visible light and even under low light intensity. Among these structures, naphthalimides, [40,[52][53][54][55][56][57][58][59][60][61][62] copper complexes, [63][64][65][66][67][68][69][70][71][72][73] flavones, [20,74] iron complexes, [75][76][77][78][79] iodonium salts, [80][81][82] coumarins, [83][84][85][86][87][88][89], acridine-1,8dione, [90][91] iridium complexes, [92][93][94][95][96][97]…”

Section: Figurementioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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Photoinitiators of polymerization with reversible electrochemical properties are actively researched as these molecules can advantageously be used in photocatalytic systems, enabling to reduce the photoinitiators content within the photocurable resins. In this field, ferrocene which is extensively used by electrochemists as a reference compound for cyclic voltammetry also exhibits a significant absorption in the visible range as well as a low oxidation potential so that this metallocene was used as a potential candidate for the design of photoinitiators of polymerization. Over the years, ferrocene has been examined in numerous polymerization processes going from anionic to cationic polymerizations, but also for the freeradical polymerization of acrylates or as a sacrificial electron donor in free radical polymerization processes. Parallel to this, the development of cheap, compact and energysaving irradiation setups based on light-emitting diodes (LEDs) have clearly favored the development of visible light photoinitiators and this technology has nowadays the potential to replace the well-established UV photopolymerization. In this review, an overview of the recent development of the ferrocene-based photoinitiating systems is provided. To evidence the interest of the ferrocene derivatives recently developed, comparisons with benchmark photoinitiators will be provided.

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Section: Figurementioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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“…The typical conversion‐time plots for the polymerization of HDDA in laminate in the presence of SND‐MAs and ND‐PM on the irradiation of LED @405 nm (I=40 mW cm −2 ) are shown in Figure a. The polymerization profiles (Figure a) verify that these macrophotoinitiators could efficiently initiate the polymerization of HDDA, and the final conversion of double bonds is up to 70 % after 15 min of visible irradiation . Among them SND‐MA‐I‐4 has a lowest final conversion (71 %).…”

Section: Resultsmentioning

confidence: 89%

Naphthalimide‐and Methacrylate‐Functionalized Polysiloxanes: Visible‐Light Photoinitiators, Modifiers for Polyurethane Acrylate and Photocurable Coatings

et al. 2018

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Employing "green chemistry" photopolymerization techniques, a series of multifunctionalized macrophotoinitiators (SND-MAs) containing naphthalimide (ND), methacrylate (MA) and polysiloxane were successfully prepared. The introduction of methacrylate enhances their compatibility with acrylate monomers and resins. SND-MAs showed very good photoinitiating properties in the presence or absence of hydrogen donors. The migration study demonstrates that SND-MAs possess excellent migration stability. In particular, the mass fractions of the extracted SND-MA-I-3 and SND-MA-I-4 in the cured 1,6-hexanediol diacrylate (HDDA) polymer are as low as 0.082 % and 0.054 %, respectively. More importantly, the use of SND-MAs as initiators brings about desirable modifications to the cured materials, such as an improved resistance against water and ethanol as well as improved thermal stability. Moreover, the series of SND-MA-Is exhibit good self-forming properties. Their self-forming films show excellent thermal properties, hardness and hydrophobicity. Thus, SND-MAs could be used as photoinitiators, modifiers and coatings at the same time.

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“…A breakthrough can be achieved by using chromophores other than phenyl or naphthalene so that the absorption spectra can be clearly displace towards the visible region, what is possible with naphthalimides. Choice of this chromophore was supported by previous works done by our groups evidencing nahphtalimide to be an excellent candidate for the design of type II photoinitiators [50][51][52][53][54][55][56][57][58][59][60].…”

Section: Introductionmentioning

confidence: 96%

Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes

et al. 2019

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Iodonium salts are well established photoacid generators, cationic photoinitiators, as well as additives commonly used in photoredox catalytic cycles. However, as a strong limitation, iodonium salts are characterized by low light absorption properties for λ > 300 nm so that these latter cannot be activated with cheap, safe, and eco-friendly near UV or even visible light emitting diodes (LEDs). To overcome this drawback, the covalent linkage of an iodonium salt to a chromophore absorbing at longer wavelength is actively researched. With aim at red-shifting the absorption spectrum of the iodonium salt, the synthesis of new compounds combining within a unique chemical structure both the chromophore (here the naphthalimide scaffold) and the iodonium salt is presented. By mean of this strategy, a polymerization could be initiated at 365 nm with the modified iodonium salts whereas no polymerization could be induced with the benchmark iodonium salt i.e., Speedcure 938 at this specific wavelength. To examine the effect of the counter-anion on the photoinitiating ability of these different salts, five different counter-anions were used. Comparison between the different anions revealed the bis(trifluoromethane)sulfonimide salt to exhibit the best photoinitiating ability in both the free radical polymerization of acrylates and the cationic polymerization of epoxides. To support the experimental results, molecular orbital calculations have been carried out. By theoretical calculations, the initiating species resulting from the photocleavage of the iodonium salts could be determined. The cleavage selectivity and the photochemical reactivity of the new iodoniums are also discussed.

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Naphthalimide‐Tertiary Amine Derivatives as Blue‐Light‐Sensitive Photoinitiators

Cited by 47 publications

References 46 publications

Recent advances on ferrocene-based photoinitiating systems

Recent advances on ferrocene-based photoinitiating systems

Naphthalimide‐and Methacrylate‐Functionalized Polysiloxanes: Visible‐Light Photoinitiators, Modifiers for Polyurethane Acrylate and Photocurable Coatings

Design of Iodonium Salts for UV or Near-UV LEDs for Photoacid Generator and Polymerization Purposes

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