Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing

Chen, Hong; Noirbent, Guillaume; Liu, Shaohui; Brunel, Damien; Graff, Bernadette; Gigmès, Didier; Zhang, Yijun; Sun, Ke; Morlet‐Savary, Fabrice; Xiao, Pu; Dumur, Frédéric; Lalevée, Jacques

doi:10.1039/d0qm00755b

Cited by 69 publications

(58 citation statements)

References 56 publications

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“…In 2021, two bis-chalcones (chalcones 7 and 8) were prepared with ferrocene and tested in the same conditions than previously used for chalcones 1-6 (See Figure 25). [136] Figure 25. Chemical structures of chalcones1-8, the monomers, and the different additives.…”

Section: Free Radical Polymerization Using Ferrocene-based Chalconesmentioning

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: Free Radical Polymerization Using Ferrocene-based Chalconesmentioning

confidence: 99%

Recent advances on ferrocene-based photoinitiating systems

Dumur

2021

European Polymer Journal

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“…Absorption characteristics of C37-C48 in acetonitrile. In 2021, the previous trends established concerning the influence of the substitution pattern on the photoinitiating ability of bis-chalcones were confirmed by a new study [112]. In this work, four bis-chalcones (C49-C52) containing thiopyranone or benzylpiperidinone central cores were examined as photoinitiators for the free-radical polymerization of a polyethylene glycol (600) diacrylate (PEG-diacrylate) and the FRPCP of EPOX at 375 and 405 nm, respectively (see Figure 20).…”

Section: Bis-chalcones Based On Cyclic Aliphatic Ketonesmentioning

confidence: 57%

“…In 2021, a series of bis-chalcones (C60-C65) connected by mean of bis-acetyl spacers was examined as photoinitiators of polymerization (See Figure 30) [112]. However, compared to the previous strategy-which enabled the generation of photoinitiators absorbing until 430 nm-in the present case, the absorption of pyridine-based chalcones and biphenyl-based chalcones was UV-centered, the main absorption band being located at 350-370 nm (see Table 11).…”

Section: Bis-chalcones Based On Two Connected Chalconesmentioning

confidence: 99%

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Recent Advances in bis-Chalcone-Based Photoinitiators of Polymerization: From Mechanistic Investigations to Applications

Giacoletto

Dumur

2021

Molecules

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Over the past several decades, photopolymerization has become an active research field, and the ongoing efforts to develop new photoinitiating systems are supported by the different applications in which this polymerization technique is involved—including dentistry, 3D and 4D printing, adhesives, and laser writing. In the search for new structures, bis-chalcones that combine two chalcones’ moieties within a unique structure were determined as being promising photosensitizers to initiate both the free-radical polymerization of acrylates and the cationic polymerization of epoxides. In this review, an overview of the different bis-chalcones reported to date is provided. Parallel to the mechanistic investigations aiming at elucidating the polymerization mechanisms, bis-chalcones-based photoinitiating systems were used for different applications, which are detailed in this review.

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“…23,24 Subsequently, with aim at improving the polymerization efficiency, 10 bis-chalcone derivatives were also prepared, but the UV-visible spectra showed that their maximum absorption peaks basically appeared between 330 and 370 nm, which does not match to the excitation wavelength of the LED@405 nm. 25 Therefore, their polymerization effect is not fully optimized. So that, in this study, we hope to improve the absorption properties (including red-shift absorption wavelength and high molar extinction coefficient) of the bis-chalcone derivatives by adjusting the chemical skeleton to prepare photoinitiator that is more suitable for low-density visible light sources.…”

Section: Introductionmentioning

confidence: 99%

In situ generation of Ag nanoparticles during photopolymerization by using newly developed dyes‐based three‐component photoinitiating systems and the related 3D printing applications and their shape change behavior

Chen

Noirbent

Liu

et al. 2021

Journal of Polymer Science

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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 simple one-step method is proposed to generate AgNPs in situ at room temperature under air by combining the photopolymerization process with the formation process of AgNPs within a few minutes. In detailed, 12 different dyes based on 2,5-diethylene-cyclopentan-1-one were first synthesized and used as high-performance type II photoinitiator. When using in conjunction of bis-(4-tertbutylphenyl) iodonium hexafluorophosphate (Iod) and ethyl 4-dimethylaminobenzoate (EDB), they can effectively boost the free radical photopolymerization (FRP) of polyethylene glycol diacrylate (PEG-DA) and the cationic photopolymerization (CP) of 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate (EPOX) upon irradiation with LED@405 nm. Furthermore, all the formulations containing/without AgNPs can be successfully used to perform the direct laser write experiment. However, even if all of the obtained 3D patterns exhibited reversible swelling performance and shape-memory effects caused by swelling and dehydration for the access to 4D printing, the presence of AgNPs will affect these properties.

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Bis-chalcone derivatives derived from natural products as near-UV/visible light sensitive photoinitiators for 3D/4D printing

Abstract: Four series of bis-chalcone compounds based on benzylpiperidinone, tetrahydrothiopyranone, pyridine or biphenyl central part are designed and synthesized, enabling to develop ten bis-chalcones varying both by the central cores but...

Cited by 69 publications

References 56 publications

Recent advances on ferrocene-based photoinitiating systems

Recent advances on ferrocene-based photoinitiating systems

Recent Advances in bis-Chalcone-Based Photoinitiators of Polymerization: From Mechanistic Investigations to Applications

In situ generation of Ag nanoparticles during photopolymerization by using newly developed dyes‐based three‐component photoinitiating systems and the related 3D printing applications and their shape change behavior

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