Effective Singlet Oxygen Sensitizers Based on the Phenazine Skeleton as Efficient Light Absorbers in Dye Photoinitiating Systems for Radical Polymerization of Acrylates

Pyszka, Ilona; Kucybała, Zdzisław; Jędrzejewska, Beata

doi:10.3390/ma14113085

Cited by 8 publications

(9 citation statements)

References 69 publications

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“…The kinetics of photoinitiated polymerization were investigated by a microcalorimetric method [29] recording changes in the heat evolution at constant time intervals (every 1 s) during polymerization. The thermo-sensitive diode was used as a temperature sensor.…”

Section: Methodsmentioning

confidence: 99%

“…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: Methodsmentioning

confidence: 99%

Section: Effect Of Photoinitiator Structurementioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Pyszka

Jędrzejewska

2021

Materials

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“…Although the three molecules of Chart are known, their photophysics has not been extensively investigated yet. , Our findings demonstrate that the optical properties of these compounds exhibit the typical characteristics of aromatic heterocycles, which are associated with their molecular structures. PQPhen , possessing the most extended π-electron system, exhibits an absorption band at 3.17 eV, while PQ2Py and Q2Py display absorption maxima at energies that are higher by 0.52 and 0.55 eV, respectively (see Figure ).…”

Section: Resultsmentioning

confidence: 99%

Harnessing Proton-Coupled Electron Transfer for Hydrogenation of Aza-Arenes: Photochemistry of Quinoxaline Derivatives in Methanol

Morawski,

Gawryś,

Sobolewski

2023

J. Phys. Chem. A

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Three quinoxaline derivatives are investigated both experimentally and theoretically to assess their ability for the methanol oxidation and harvesting of hydrogen. In inert solvents, the nonplanar compounds exhibit very weak fluorescence from the lowest excited singlet state, whereas the planar and rigid chromophore emits non-Kasha fluorescence from the S2(ππ*) state despite the proximity of the S1(nπ*) state. In methanol, hydrogen-bonded complexes with solvent molecules are formed, and in all chromophores, the lowest singlet state is populated after excitation of the S2(ππ*) state. The switch from non-Kasha emission of the planar compound in inert solvents to regular emission in methanol is related to reduced symmetry of the hydrogen-bonded complex with methanol which results in effective mixing of ππ* and nπ* states and fast internal conversion to the lowest excited singlet state. The S1(nπ*) state of the hydrogen-bonded complex has charge-transfer character, and for all compounds in methanol, hydrogen transfer to the chromophore is observed. The chromophores retain the transferred hydrogen atoms, serving both as photocatalysts and as hydrogen storage materials. Undesired dark side reactions that occur are also discussed.

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“…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

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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.

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Effective Singlet Oxygen Sensitizers Based on the Phenazine Skeleton as Efficient Light Absorbers in Dye Photoinitiating Systems for Radical Polymerization of Acrylates

Cited by 8 publications

References 69 publications

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Harnessing Proton-Coupled Electron Transfer for Hydrogenation of Aza-Arenes: Photochemistry of Quinoxaline Derivatives in Methanol

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

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