Difluoroboranyl derivatives as efficient panchromatic photoinitiators in radical polymerization reactions

Jędrzejewska, Beata; Ośmiałowski, Borys

doi:10.1007/s00289-017-2201-1

Cited by 12 publications

(11 citation statements)

References 53 publications

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“…They usually contain ketones, aldehydes, quinones and selected dyes in combination with a tertiary amine, carboxylic acids, borate salts and others electron donors that form photoredox pairs. Radicals, which start a chain reaction, are generated from a co-initiator according to photoinduced hydrogen atom transfer [17][18][19] or electron transfer [6,[20][21][22][23][24][25][26][27][28][29][30][31] mechanism.…”

Section: Introductionmentioning

confidence: 99%

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Pyszka

Jędrzejewska

2021

Materials

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A series of dyes based on the acenaphthoquinoxaline skeleton was synthesized. Their structure was modified by introducing electron-withdrawing and electron-donating groups, increasing the number of conjugated double bonds and the number and position of nitrogen atoms, as well as the arrangement of aromatic rings (linear or angular). The dyes were investigated as a component in the photoinitiating systems of radical polymerization for a potential application in dentistry. They acted as the primary absorber of visible light and the acceptor of an electron, which was generated from a second component being an electron donor. Thus, the radicals were generated by the photoinduced intermolecular electron transfer (PET) process. Electron donors used differed in the type of heteroatom, i.e., O, S and N and the number and position of methoxy substituents. To test the ability to initiate the polymerization reaction by photoinduced hydrogen atom transfer, we used 2-mercaptobenzoxazole as a co-initiator. The effectiveness of the photoinitiating systems clearly depends on both the modified acenaphthoquinocaline structure and the type of co-initiator. The lower amount of heat released during the chain reaction and the polymerization rate comparable to this achieved for the photoinitiator traditionally used in dentistry (camphorquinone) indicates that the studied dyes may be valuable in this field.

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Section: Introductionmentioning

confidence: 99%

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Pyszka

Jędrzejewska

2021

Materials

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“…Recently, a great deal of efforts has also be devoted to develop panchromatic dyes, namely structures exhibiting a broad absorption extending over the visible range. [146][147][148][149][150] However, availability of such dyes is still limited in the literature. [41,128,147,150,151] Parallel to the light absorption properties, the way how the initiating species are produced is another key parameter to get an efficient polymerization.…”

Section: Figure 1 the Characteristic Features Of Photopolymerizationmentioning

confidence: 99%

Recent advances on chalcone-based photoinitiators of polymerization

Ibrahim‐Ouali

Dumur

2021

European Polymer Journal

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Photopolymerization is an active research field facing a revolution due to the recent availability of cheap, lightweight, compact and energy-saving light sources that constitutes light-emitting diodes (LEDs). With regards to the low light intensity delivered by these new irradiation setups, the demand for photoinitiating systems activable under low light intensity, in the visible range, and exhibiting a high reactivity even under air are actively researched.With aim at developing dyes fitting the above requirements while remaining relatively uncoloured, chalcones are one of those. In this review, an overview of the recent development concerning chalcone-based photoinitiating systems is reported. With aim at evidencing the crucial interest of this family of dyes, comparisons with benchmark photoinitiators will be presented.

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“…BODIPYs have been extensively studied as fluorescent probes for bioimaging applications [138][139][140][141] but only scarcely for the design of photoinitiators [142][143][144]. The first carbazole-based BODIPY used as photoinitiator was reported in 2019 (Cbz_35) in the context of a polymerization carried out in the near infrared region (See Fig.…”

Section: Carbazole-based Bopidysmentioning

confidence: 99%

Recent advances on carbazole-based photoinitiators of polymerization

Dumur

2020

European Polymer Journal

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Photoinitiators of polymerization that can be activated under visible light and low intensity are actively researched as these compounds constitute the next generation of photoinitiators that will replace the controverted UV-photoinitiators. Over the years, a family of compounds has been identified as being highly promising in light of its remarkable photoinitiating ability, photochemical stability, low cost and easiness to functionalize, namely carbazoles. In this review, an overview of the different carbazole-based photoinitiators reported to date is presented. Interestingly, carbazoles have mostly been used as electron donors in push-pull structures, as photosensitizers for iodonium salts, as ligands for ferrocenium salts or as chromophores for phenacyl onium salts. These different applications clearly demonstrate the versatility of this structure used as the elemental building block for the design of UV, near-UV or visible light photoinitiators.

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Difluoroboranyl derivatives as efficient panchromatic photoinitiators in radical polymerization reactions

Cited by 12 publications

References 53 publications

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Recent advances on chalcone-based photoinitiators of polymerization

Recent advances on carbazole-based photoinitiators of polymerization

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