Effect of substituents on the performance of N-carbazolyl double benzylidene ketones in visible/NIR light one/two-photon polymerization

Xie, Jie; Wang, Xiaobing; Wang, Yonghui; Li, Jiawei; Cao, Chun; Jin, Ming

doi:10.1016/j.eurpolymj.2023.112636

Cited by 2 publications

(1 citation statement)

References 52 publications

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“…Recently, such PIs containing heterocycles/heteroatoms have also been used in the field of nanotechnology, especially for two-photon lithography. − Two-photon lithography is an additive manufacturing technology based on two-photon polymerization (TPP), leveraging nonlinear and super-resolution concepts to achieve precise 3D printing with a single tightly focused laser beam . This method shows application potential in various fields such as microrobotics, biomaterials, and tissue engineering. − The commercial two-photon PI DETC (7-diethylamino-3-thienylcoumarin), which contains thiophene, has been commonly used in TPP. , Cao et al designed and synthesized a series of heteroatom-substituted ketocoumarins as PIs, and these compounds exhibit high sensitivity in two-photon lithography, which allows for the fabrication of complex three-dimensional patterns at writing speeds of up to 60 mm s –1 .…”

Section: Introductionmentioning

confidence: 99%

Heteroatom/Heterocycle-Substituted Ketone Dyes as Efficient Photoinitiators in Visible Light-Emitting Diode/Near Infrared Light Photopolymerization with Enhanced Two-Photon Lithography Capability

Guo,

Zhou,

Fan

et al. 2024

ACS Appl. Polym. Mater.

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Photopolymerization is a burgeoning technology with a wide range of applications from coatings and inks to nanotechnology. The development of photosensitized systems that can work at long wavelengths with safety and environmental friendliness, such as visible light-emitting diodes and near infrared light, is essential. In this study, a series of ketone dyes containing heteroatom/heterocyclic substituents were designed on the basis of the carbazole−coumarin backbone to compare with aryl ring-substituted ones. The photophysical and photochemical properties of the dyes were studied by UV−vis spectroscopy, time-dependent density functional theory calculations, fluorescence spectroscopy, and steady-state photolysis. The potential application of dyes in one/two-photon polymerization was investigated. Results showed that the introduction of heterocycles/heteroatoms has a considerable influence on the absorption and polymerization properties of dyes. CCK−Th, which contains a thiophene substitute, exhibits the most excellent light absorption properties as well as the fastest reaction efficiency with amine additives. Notably, when comparing the two-photon lithography capability, the photoresist containing 0.1 wt % CCK− Th, which can achieve a writing speed of 46 mm s −1 , exhibits high two-photon sensitivity, about two times that of the benzene ringsubstituted CCK−Ben. In addition, CCK−Th shows outstanding ability to construct complex three-dimensional patterns. These modified CCKs show great application potential in nanotechnology, additive manufacturing, and optoelectronics and provide design concepts for the development of photoinitiators.

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Section: Introductionmentioning

confidence: 99%

Heteroatom/Heterocycle-Substituted Ketone Dyes as Efficient Photoinitiators in Visible Light-Emitting Diode/Near Infrared Light Photopolymerization with Enhanced Two-Photon Lithography Capability

Guo,

Zhou,

Fan

et al. 2024

ACS Appl. Polym. Mater.

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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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Effect of substituents on the performance of N-carbazolyl double benzylidene ketones in visible/NIR light one/two-photon polymerization

Cited by 2 publications

References 52 publications

Heteroatom/Heterocycle-Substituted Ketone Dyes as Efficient Photoinitiators in Visible Light-Emitting Diode/Near Infrared Light Photopolymerization with Enhanced Two-Photon Lithography Capability

Heteroatom/Heterocycle-Substituted Ketone Dyes as Efficient Photoinitiators in Visible Light-Emitting Diode/Near Infrared Light Photopolymerization with Enhanced Two-Photon Lithography Capability

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

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