Recent advances on anthracene-based photoinitiators of polymerization

Dumur, Frédéric

doi:10.1016/j.eurpolymj.2022.111139

Cited by 20 publications

(13 citation statements)

References 317 publications

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“…[18,19] Nevertheless, these OXEs only absorb for rather short wavelengths and their performances decline with increasing wavelength using, e.g., near UV LEDs (385 and 395 nm) or visible LEDs (405, 415, 450 nm). Hence, recent research studies have been focused on shifting the absorption wavelength of OXEs to the near UV or visible range by introducing different chromophores into their structures (triphenylamine, [20] coumarin, [21] nitrocarbazole, [22] anthracene, [23] pyrene, [24] phenothiazine, [25] etc. ).…”

Section: Introductionmentioning

confidence: 99%

Photoinitiation Mechanisms of Novel Phenothiazine‐Based Oxime and Oxime Esters Acting as Visible Light Sensitive Type I and Multicomponent Photoinitiators

Noon

Hammoud

Graff

et al. 2023

Adv Materials Technologies

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In this work, three new photoinitiators, based on the phenothiazine scaffold as a chromophore and potentially bearing the oxime ester functionality as an initiating group are designed and synthesized for the free radical polymerization of acrylates, the cationic polymerization of epoxides, and the formation of interpenetrated polymer networks upon irradiation with a light emitting diode emitting at 405 nm. These phenothiazine‐based oxime and oxime esters revealed impressive photoinitiation ability manifested by excellent polymerization rates and high final reactive function conversions. Significantly, they can be used as both; one‐component (Type I) and two‐component photoinitiating systems. Photoinitiation mechanisms through which reactive species are produced are investigated by means of different complementary techniques including real‐time Fourier transform infrared spectroscopy, UV–visible absorption spectroscopy, electron spin resonance spectroscopy, fluorescence (steady state and time resolved), cyclic voltammetry, and molecular modeling calculations. Thermal initiation behavior of the different oxime esters is also studied by using differential scanning calorimetry, highlighting their dual thermal/photochemical initiation ability. Finally, 3D printed objects are successfully fabricated by conducting both direct laser writing and 3D printing experiments.

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Section: Introductionmentioning

confidence: 99%

Photoinitiation Mechanisms of Novel Phenothiazine‐Based Oxime and Oxime Esters Acting as Visible Light Sensitive Type I and Multicomponent Photoinitiators

Noon

Hammoud

Graff

et al. 2023

Adv Materials Technologies

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“…The collected data align well with similar anthracene derivatives described in the literature. [ 77 ] Furthermore, all of these systems, namely NAK, TAK, and DTAK chromophores, display a notable photoluminescence (PL) band, represented by dashed lines in Figure 6, situated in the visible range, specifically between 400 and 700 nm. The PL maxima vary from 493.2 nm for DTAK dye up to the 503.8 nm for TAK one, respectively, which is the reddest shifted emission among the considered chromophores.…”

Section: Resultsmentioning

confidence: 99%

Unveiling All‐Optical Switching Phenomenon in Anthracene Derivatives: A Comprehensive Study on Optical and Nonlinear Optical Multifunctionality

Szukalski,

Zajac,

Pardus

et al. 2024

Advanced Optical Materials

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In this study, it is considered three anthracene derivatives, characterized meticulously in terms of their chemical structure and product purity. Extensive quantum chemical calculations are conducted to elucidate their optical and nonlinear optical properties, shedding light on the mechanism of photoinduced conformational transformation, a pivotal discovery in this research. Experimental analyses encompassed fundamental optical properties and advanced nonlinear optical phenomena, including z‐scan experiments, second harmonic generation (SHG), and third harmonic generation (THG). Remarkably, a groundbreaking all‐optical switching phenomenon in these materials is experimentally validated, marking a significant advancement and contributing to their potential applications.

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“…However, the use of UV-absorbing photoinitiators/photosensitizers has raised some toxicity issues and prompted researchers to synthesize new red-shifted absorbing photoinitiating systems. To date, various photoinitiators have been designed to extend their absorbance spectra in the visible or IR range [ 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 ]. This stems from the fact that visible or IR light is not only safer than UV light but also presents a higher penetration capability, despite the use of UV-absorbing monomers, substrates, and pigments.…”

Section: Introductionmentioning

confidence: 99%

Thioxanthone-Based Siloxane Photosensitizer for Cationic/Radical Photopolymerization and Photoinduced Sol–Gel Reactions

Nguyen,

Breloy,

Rios De Anda

et al. 2024

Molecules

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In this investigation, a multifunctional visible-light TX-based photosensitizer containing a siloxane moiety (TXS) was designed with a good overall yield of 54%. The addition of a siloxane moiety enabled the incorporation of a TX photosensitizer into a siloxane network by photoinduced sol–gel chemistry, thus avoiding its release. Both liquid 1H and solid-state 29Si NMR measurements undeniably confirmed the formation of photoacids resulting from the photolysis of the TXS/electron acceptor molecule (Iodonium salt), which promoted the photoinduced hydrolysis/condensation of the trimethoxysilane groups of TXS, with a high degree of condensation of its inorganic network. Notably, the laser flash photolysis, fluorescence, and electron paramagnetic resonance spin-trapping (EPR ST) experiments demonstrated that TXS could react with Iod through an electron transfer reaction through its excited states, leading to the formation of radical initiating species. Interestingly, the TXS/Iod was demonstrated to be an efficient photoinitiating system for free-radical (FRP) and cationic (CP) polymerization under LEDs@385, 405, and 455 nm. In particular, whatever the epoxy monomer mixtures used, remarkable final epoxy conversions were achieved up to 100% under air. In this latter case, we demonstrated that both the photoinduced sol–gel process (hydrolysis of trimethoxysilane groups) and the cationic photopolymerization occurred simultaneously.

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Recent advances on anthracene-based photoinitiators of polymerization

Cited by 20 publications

References 317 publications

Photoinitiation Mechanisms of Novel Phenothiazine‐Based Oxime and Oxime Esters Acting as Visible Light Sensitive Type I and Multicomponent Photoinitiators

Photoinitiation Mechanisms of Novel Phenothiazine‐Based Oxime and Oxime Esters Acting as Visible Light Sensitive Type I and Multicomponent Photoinitiators

Unveiling All‐Optical Switching Phenomenon in Anthracene Derivatives: A Comprehensive Study on Optical and Nonlinear Optical Multifunctionality

Thioxanthone-Based Siloxane Photosensitizer for Cationic/Radical Photopolymerization and Photoinduced Sol–Gel Reactions

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