Fused carbazole–coumarin–ketone dyes: high performance and photobleachable photoinitiators in free radical photopolymerization for deep photocuring under visible LED light irradiation

Guo, Xinyue; Mao, Huanv; Wan, Decheng; Jin, Ming

doi:10.1039/d2py00466f

Cited by 27 publications

(19 citation statements)

References 62 publications

(69 reference statements)

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“…Reproduced with permission of Ref. [190] Occurrence of a photobleaching process was confirmed during the FRP of various acrylate monomers such as TMPTA, HDDA or tri(propylene glycol) diacrylate (TPGDA).…”

Section: Figure 31mentioning

confidence: 98%

“…Coumarins have been extensively studied as visible light photoinitiators of polymerization due to their exceptional reactivity. [187][188][189][190][191][192] In light of this reactivity, various derivatives were designed and synthesized such as iodonium salts, [98] oxime esters, [193] water soluble structures, [194] or fused carbazole-coumarin hybrid structures. [190] Coumarins are versatile structures and more than 100 structures were reported in the literature, these structures being combined with different additives.…”

Section: Coumarinsmentioning

confidence: 99%

“…[187][188][189][190][191][192] In light of this reactivity, various derivatives were designed and synthesized such as iodonium salts, [98] oxime esters, [193] water soluble structures, [194] or fused carbazole-coumarin hybrid structures. [190] Coumarins are versatile structures and more than 100 structures were reported in the literature, these structures being combined with different additives. [187,188,[193][194][195][196][197][198][199][200][201][202][203] Different structures exhibiting photobleaching properties were identified.…”

Section: Coumarinsmentioning

confidence: 99%

“…Finally, hybrid structures based on the carbazole/coumarin combination and the carbazole/coumarin/benzophenone combinations were successfully obtained and proved to be photobleachable photoinitiating systems (See Figure 34). [190] Figure 34. Chemical structures of C32-C34.…”

Section: Figure 31mentioning

confidence: 99%

“…Figure 35. Mechanism of photoinitiation also enabling an efficient photobleaching of the polymers.Reproduced with permission of Ref [190]. …”

mentioning

confidence: 99%

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Recent advances on photobleachable visible light photoinitiators of polymerization

Dumur

2023

European Polymer Journal

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Section: Figure 31mentioning

confidence: 98%

Section: Coumarinsmentioning

confidence: 99%

Section: Coumarinsmentioning

confidence: 99%

Section: Figure 31mentioning

confidence: 99%

“…Figure 35. Mechanism of photoinitiation also enabling an efficient photobleaching of the polymers.Reproduced with permission of Ref [190]. …”

mentioning

confidence: 99%

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Recent advances on photobleachable visible light photoinitiators of polymerization

Dumur

2023

European Polymer Journal

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Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

Xie,

Huang,

et al. 2023

Applied Research

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Photopolymerization of thiol–epoxy resins initiated by photobase generators (PBGs) is a very good way to prepare specific polymeric products. However, lack of near‐UV or visible LED light sensitive PBGs that can release strong bases to effectively catalyze this reaction and synchronously monitor the polymerization progress still is a problem. In this work, a series of such PBGs are successfully synthesized by modifying common AIE molecules including triphenylamine (TPA) and tetraphenylethylene (TPE) and then neutralizing them with strong bases like 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU), 1,5‐diazabicyclo[4.3.0]non‐5‐ene(DBN) and 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene (TBD). The obtained PBGs show very good light absorption ability from 365 to 405 nm. They can generate free strong bases under near‐UV/visible LED light radiations as a result of photodecarboxylation reaction to catalyze the rapid thiol‐epoxy photopolymerization. The TBD‐based PBGs have the best final monomer conversion above 60% due to their strongest alkalinity. Increasing viscosity during the polymerization process can trigger an AIE phenomenon of the PBGs. A linear correlation equation of the AIE intensity with the monomer conversion can be founded, which is helpful for quantitatively monitoring the photopolymerization progress. More importantly, qualitative observations of the brightness changes of the resulting AIE lights are very useful to visualize the photopolymerization progress, which may find some applied potentials in industry.This article is protected by copyright. All rights reserved.

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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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Fused carbazole–coumarin–ketone dyes: high performance and photobleachable photoinitiators in free radical photopolymerization for deep photocuring under visible LED light irradiation

Abstract: In this work, three dyes based on fused carbazole–coumarin–ketone structures were designed and synthesized. These dyes were named CCK–Me, CCK–Ph, and CCK–Tol in accordance with their different substituents. Their excellent...

Cited by 27 publications

References 62 publications

Recent advances on photobleachable visible light photoinitiators of polymerization

Recent advances on photobleachable visible light photoinitiators of polymerization

Photobase generators with AIE property used for visual observations of thiol–epoxy near‐UV/visible photopolymerization

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

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