Stilbene-benzophenone dyads for free radical initiating polymerization of methyl methacrylate under visible light irradiation

Qin, Xiaozhuan; Ding, Ge; Gong, Yulong; Jing, Chuan; Peng, Guangyue; Liu, Shihong; Niu, Lianbin; Zhang, Shengtao; Luo, Zundu; Li, Hongru; Gao, Fang

doi:10.1016/j.dyepig.2016.04.035

Cited by 23 publications

(5 citation statements)

References 30 publications

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“…From Figure , it is also seen, that as soon as the photoinitiating polymerization rates observed for SQ/NO2 system reached the peak values, a gradual decrease was observed with the extension of visible light irradiation time at the different concentrations of the photoinitiators. Basing on the Gao and coworkers studies those observations may be ascribed to the following factors: (i) the photoinitiating polymerization systems were consumed, (ii) the photopolymer formed increases the viscosity of the system, and the photoinitiating polymerization reaction could be inhibited accordingly, (iii) the coupling rate of free radicals increased as more radicals were obtained . The chemical structure of N ‐alkoxypyridinum salt influences also on the kinetics of polymerization of triacrylate.…”

Section: Resultsmentioning

confidence: 99%

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N‐alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties

Kabatc

Kostrzewska

Dobosz

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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A few N-alkoxypyridinium salts are developed as photoinitiators for efficient polymerization reactions. They are characterized by absorption properties below 300 nm, and generate alkoxy radicals on UV-Vis light exposure. The squarylium dye was used as a blue-light photosensitizer. Polymerization results are correlated with the photochemistry of N-alkoxypyridinium salts. The quenching of the excited singlet state of squarylium dye by pyridinium salt and the formation of the semioxidized species of squaraine suggests an electron transfer from an excited dye to a coinitiator, and that the resulting oxygen-centered radical initiates the polymerization process.The chemical mechanism was investigated by steady state photolysis and nanosecond laser flash photolysis experiments. Photoinitiating activity of new photoinitiators for initiation of polymerization of trimethylolpropane triacrylate in the UV-blue light region was compared with photoinitiating ability of selected commercially available initiators.

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Section: Resultsmentioning

confidence: 99%

“…The fluorescence lifetimes of 1,3‐bis( p ‐bromophenylamino)squaraine in MP are about 2.69 and 10.76 ns. The longer fluorescence lifetime may be attributed to the first singlet excited state of the most stable conformer of the photosensitizer …”

Section: Resultsmentioning

confidence: 99%

N‐alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties

Kabatc

Kostrzewska

Dobosz

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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“…Benzophenone derivatives are commonly used as Type II photoinitiators after the chemical modifications of them have been performed by moieties such as triphenylamine [55], carbazole [56], stilbene [57], and naphthalimide [58]. As possible hydrogen acceptors, benzophenone derivatives are often paired with other co-initiators acting as hydrogen donors to proceed with the electron/proton transfer.…”

Section: Benzophenone Derivativesmentioning

confidence: 99%

3D Printing/Vat Photopolymerization of Photopolymers Activated by Novel Organic Dyes as Photoinitiators

et al. 2022

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Even though numerous organic dyes which are used as photoinitiators/photocatalysts during photopolymerization have been systematically investigated and collected in previous reviews, further designs of these chromophores and the developments in high-performance photoinitiating systems have emerged in recent years, which play the crucial role in 3D printing/Vat polymerization. Here, in this mini-review, various families of organic dyes that are used as newly synthesized photoinitiators/photocatalysts which were reported in literature during 2021–2022 are specified by their photoinitiation mechanisms, which dominate their performance during photopolymerization, especially in 3D printing. Markedly, visible light-induced polymerization could be employed in circumstances not only upon the irradiation of artificial light sources, e.g., in LEDs, but also in sunlight irradiation. Furthermore, a short overview of the achievements of newly developed mechanisms, e.g., RAFT, photoinitiator-RAFT, and aqueous RAFT using organic chromophores as light-harvesting compounds to induce photopolymerization upon visible light irradiation are also thoroughly discussed. Finally, the reports on the semiconducting nanomaterials that have been used as photoinitiators/photocatalysts during photopolymerization are also introduced as perspectives that are able to expand the scope of 3D printing and materials science due to their various advantages such as high extinction coefficients, broad absorption spectra, and having multiple molecular binding points.

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“…[18][19][20] However, considering that these chromophores were UVcentered, shift of their absorptions towards the visible range can only be obtained at the cost of difficult syntheses and most of the dyes only absorb not far from the near-UV/visible range. [21][22][23][24][25][26][27][28][29] Face to these considerations, a second approach consists in developing new molecules totally disconnected from these historical structures. [30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47][48] Considering that visible light photoinitiators of polymerization should exhibit a strong absorption over the visible range, long-living excited state lifetimes but also appropriate electrochemical properties in order to efficiently interact with the different additives introduced into the photocurable resins, structures commonly used in Organic Electronics are candidates of choice for photoinitiation.…”

Section: Introductionmentioning

confidence: 99%

Chemical engineering around the 5,12-dihydroindolo[3,2-a]carbazole scaffold: Fine tuning of the optical properties of visible light photoinitiators of polymerization

Hammoud

Hijazi

Ibrahim‐Ouali

et al. 2022

European Polymer Journal

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Stilbene-benzophenone dyads for free radical initiating polymerization of methyl methacrylate under visible light irradiation

Cited by 23 publications

References 30 publications

N‐alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties

N‐alkoxypyridinium salts as coinitiators in radical polymerization: Synthesis and Photochemical Properties

3D Printing/Vat Photopolymerization of Photopolymers Activated by Novel Organic Dyes as Photoinitiators

Chemical engineering around the 5,12-dihydroindolo[3,2-a]carbazole scaffold: Fine tuning of the optical properties of visible light photoinitiators of polymerization

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