Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

Strzelczyk, Rafał

doi:10.1111/cote.12266

Cited by 12 publications

(6 citation statements)

References 31 publications

(65 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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

View full text Add to dashboard Cite

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.

show abstract

Section: Introductionmentioning

confidence: 99%

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Pyszka

Jędrzejewska

2021

Materials

View full text Add to dashboard Cite

show abstract

“…The values of E ox and E red are determined from cyclic voltammetry (Figure S8, Supporting Information). The energy of the excited singlet state, E S , could be calculated by the intersection of normalized absorption and emission spectra (Figure S9, Supporting Information) . The E ox , E red , and E S (or E T )values of ND‐O‐EA are summarized in Table 2 .…”

Section: Resultsmentioning

confidence: 99%

“…The energy of the excited singlet state, E S , could be calculated by the intersection of normalized absorption and emission spectra ( Figure S9, Supporting Information). [19,20] The E ox , λ max is the maximum absorption wavelength in acetonitrile solution; b) ε is the molar absorptivity value at λ max ; c) ε 405 is the molar absorptivity value at λ 405nm ; d) ε 455 is the molar absorptivity value at λ 455nm ; e) ε 470 is the molar absorptivity value at λ 470nm . Table 2.…”

Section: Uv-vis Absorptionmentioning

confidence: 96%

A Green and Highly Efficient Naphthalimide Visible Photoinitiator with an Ability Initiating Free Radical Polymerization under Air

Yang

Xiong

et al. 2018

Macro Chemistry & Physics

View full text Add to dashboard Cite

A visible photoinitiator, 2‐(2‐(1,3‐dioxo‐6‐(piperidin‐1‐yl)‐1H‐benzo[de]‐isoquinolin‐2(3H)‐yl)ethoxy)ethyl acrylate (ND‐O‐EA), for attenuating the oxygen inhibition in the free radical polymerization, is designed and synthesized. The results show that it has an outstanding ability to overcome oxygen inhibition demonstrated by the fact that no induction period is observed during the free radical polymerization of the acrylate in the air. A possible preferred intramolecular hydrogen‐abstraction reaction in which a peroxyl radical regenerates a new carbon radical through a stable six‐member ring intermediate, should correspond to its anti‐oxygen capacity. After 1 min of irradiation under air atmosphere, the double‐bond conversion of 1,6‐hexanediol diacrylate in the ND‐O‐EA system can be up to 13.3%, while the camphorquinone‐N‐methyldiethanolamine (CQ‐MDEA) system is about 8.0%, and the phenylbis(2,4,6‐trimethylbenzoyl)phosphine oxide (BAPO) is only 0.13%. Furthermore, as a one‐component polymerizable photoinitiator, the mass fraction of the extracted ND‐O‐EA is about 6.2% with respect to the initial quality after photopolymerization.

show abstract

“…Type II photoinitiators generate radicals in the electron transfer process (PET) between the photoinitiator and co-initiator [ 33 , 34 , 35 , 36 , 37 ], or in the hydrogen-atom transfer process [ 37 , 38 , 39 ]. Type II photoinitiators include aromatic ketones, such as benzophenone [ 40 ], thioxanthone [ 41 ], ketocoumarin [ 42 ], and their derivatives, as well as α-diketones (e.g., camphorquinone) [ 43 , 44 , 45 ] and various dyes: cyanines [ 46 ], phenazines [ 47 ], quinoxalines [ 37 ], and many others [ 36 , 48 , 49 , 50 , 51 , 52 ]. Co-initiators are compounds that react with an excited initiator, resulting in the formation of a radical capable of initiating free-radical polymerization.…”

Section: Introductionmentioning

confidence: 99%

Highly Efficient Photoinitiation Systems Based on Dibenzo[a,c]phenazine Sensitivity to Visible Light for Dentistry

Pyszka,

Jędrzejewska

2024

Materials

View full text Add to dashboard Cite

In this work, photoinitiation systems based on dibenzo[a,c]phenazine sensitivity to visible light were designed for their potential application in dentistry. Modification of the structure of dibenzo[a,c]phenazine consisted of introducing electron-donating and electron-withdrawing substituents and heavy atoms into position 11. The synthesized compounds are able to absorb radiation emitted by dental lamps during photoinitiation of the polymerization process. In the presence of acrylates, dibenzo[a,c]phenazines show excellent photoinitiating abilities in systems containing an electron donor or a hydrogen-atom donor as a second component. The developed systems initiate the polymerization process comparable to a commercial photoinitiator, i.e., camphorquinone. Moreover, the performed studies showed a significant shortening of the polymerization time and a reduction in the amount of light absorber. This indicates that polymeric materials are obtained at a similar rate despite a significant reduction in the concentration of the newly developed two-component photoinitiating systems.

show abstract

Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

Cited by 12 publications

References 31 publications

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

A Green and Highly Efficient Naphthalimide Visible Photoinitiator with an Ability Initiating Free Radical Polymerization under Air

Highly Efficient Photoinitiation Systems Based on Dibenzo[a,c]phenazine Sensitivity to Visible Light for Dentistry

Contact Info

Product

Resources

About