New-generation ketoxime ester-type photoinitiator model molecules: Improving photoactivity by introducing o-allyloxy group

Liao, Wen; Jin, Ming

doi:10.1016/j.porgcoat.2024.108290

Progress in Organic Coatings

2024

DOI: 10.1016/j.porgcoat.2024.108290

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New-generation ketoxime ester-type photoinitiator model molecules: Improving photoactivity by introducing o-allyloxy group

Wen Liao,

Ming Jin

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2024

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Cited by 4 publications

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High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

Zhang,

Song,

Liu

et al. 2024

Angewandte Chemie

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In this work, six benzothioxanthene‐based oxime esters were employed as photoinitiators for photopolymerization with visible light (LED) and sunlight. Their abilities to behave as Type I photoinitiators by mean of a photocleavage mechanism of oxime esters but also in multicomponent photoinitiating system with an iodonium salt (through an electron transfer mechanism) were both explored with the different structures. Due to their broad absorption spectra tailing up 600 nm, photoinitiating properties of the benzothioxanthene‐based oxime esters were systematically tested under excitation with low‐intensity LED light at wavelengths of 405 nm and 450 nm. Additionally, to the polymerization tests done under artificial light, different benzothioxanthene‐based oxime esters were also investigated as solar photoinitiators and displayed a high reactivity in France (Western Europe) even in winter conditions. For the best candidates i.e. the most reactive structures, direct laser write experiments were carried out, evidencing the interest of these structures.

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High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

Zhang,

Song,

Liu

et al. 2024

Angewandte Chemie

View full text Add to dashboard Cite

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High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

Zhang,

Song,

Liu

et al. 2024

Angew Chem Int Ed

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Enhanced One/Two‐Photon Initiating Performance of Nitro‐Carbazole‐Styrene Based Oxime/Ketoxime Esters

Xie,

Wang,

Wang

et al. 2024

Chin. J. Chem.

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Comprehensive SummaryPhotoinitiators of the oxime ester (OXE) or ketoxime ester (OXE‐CO) type can rapidly undergo N—O bond cleavage and generate free radicals to initiate photopolymerization under LED excitation, occupying an important position in the field of photocuring. However, the commercial OXEs, e.g., OXE 01 and 02 with λmax's at 326 and 344 nm, respectively, still do not well match the emission spectra of LEDs. Developing novel OXEs/OXE‐COs with high photosensitivity for long‐wavelength LEDs has great significance. Here, four new OXEs/OXE‐COs with nitro‐carbazole‐styrene conjugated chromophore were designed, synthesized, and used as photoinitiators. Results demonstrated that all photoinitiators had strong absorption within the UV–vis range (λmax: 381—392 nm, εmax: 8200—11500 M−1·cm−1). Molecular design of the oxime ester cleavage to produce a small volume methyl group and a methacryl group with an unsaturated double bond brings high activity and low migration, respectively, in one‐photon polymerization under 365—450 nm LEDs excitation. Moreover, OXEs/OXE‐COs with PETA exhibited a wide processing window, high resolution (line accuracy~100 nm) and good nano‐patterning capability under 780 nm femtosecond laser irradiation in two‐photon polymerization, indicating their great potential in 2D/3D microfabrication technologies.

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New-generation ketoxime ester-type photoinitiator model molecules: Improving photoactivity by introducing o-allyloxy group

Cited by 4 publications

References 45 publications

High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

High Photoinitiating Efficiency of Benzothioxanthene‐Based Oxime Esters in Photopolymerization via Photocleavage and/or Single Electron Transfer under Visible Light and Sunlight

Enhanced One/Two‐Photon Initiating Performance of Nitro‐Carbazole‐Styrene Based Oxime/Ketoxime Esters

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