Highly Effective Sensitizers Based on Merocyanine Dyes for Visible Light Initiated Radical Polymerization

Jędrzejewska, Beata; Wejnerowska, Grażyna

doi:10.3390/polym12061242

Cited by 12 publications

(11 citation statements)

References 49 publications

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“…This is fully confirmed by the data shown in Figure 6 for two sensitizers AN3 and AN6. The choice of electron donors was based on our previous research on the photoinitiated polymerization process [19,23,29,72,73]. In order to evaluate the effect of the different co-initiators on the photoinitiating abilities of the tested photoredox pairs, PhAA was used as a benchmark electron donor.…”

Section: Effect Of Photoinitiator Structurementioning

confidence: 99%

“…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%

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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: Effect Of Photoinitiator Structurementioning

confidence: 99%

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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“…Firstly, through a simple Knoevenagel condensation reaction, the D-π-A molecular DBDT with red light emission could be obtained (The detailed synthesis procedure and photophysical data had been reported by Hong's group and Jedrzejewska's group). [40,41] In this study, we mainly focused on the properties and application of needle-like crystals. Secondly, the long needlelike crystals (centimeter-scale)(Figure S2) could be prepared in DCM/CH 3 OH (v/v = 2/8).…”

Section: Introductionmentioning

confidence: 99%

Elastic Organic Crystals Based on Barbituric Derivative: Multi‐faceted Bending and Flexible Optical Waveguide

Peng

Bai

Cao

et al. 2021

Chemistry A European J

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Elastic organic single crystals with light-emitting and multi-faceted bending properties are extremely rare. They have potential application in optical materials and have attracted the extensive attention of researchers. In this paper, we reported a structurally simple barbituric derivative DBDT, which was easily crystallized and gained long needle-like crystals (centimeter-scale) in DCM/CH 3 OH (v/v = 2/8). Upon applying or removing the mechanical force, both the ( 100) and ( 040) faces of the needle-like crystal showed reversible bending behaviour, showing the nature of multi-faceted bending. The average hardness (H) and elastic modulus (E) were 0.28 � 0.01 GPa and 4.56 � 0.03 GPa for the (040) plane, respectively. Through the analysis of the single crystal data, it could be seen that the van der waals (CÀ H•••π and CÀ H•••C), Hbond (CÀ H•••O) and π•••π interactions between molecules were responsible for the generation of the crystal elasticity.Interestingly, elastic crystals exhibited optical waveguide characteristics in straight or bent state. The optical loss coefficients measured at 627 nm were 0.7 dBmm À 1 (straight state) and 0.9 dBmm À 1 (bent state), while the optical loss coefficient (α) were 1.5 dBmm À 1 (straight state) and 1.8 dBmm À 1 (bent state) at 567 nm. Notably, the elastic organic molecular crystal based on barbituric derivative could be used as the candidate for flexible optical devices.

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Highly Effective Sensitizers Based on Merocyanine Dyes for Visible Light Initiated Radical Polymerization

Cited by 12 publications

References 49 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

Elastic Organic Crystals Based on Barbituric Derivative: Multi‐faceted Bending and Flexible Optical Waveguide

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