Synthesis and photochemical reaction of benzo[<i>a</i>]quinoxalino[2,3‐<i>c</i>]phenazine dyes

Sokołowska, Jolanta; Kolińska, Jolanta; Grzelakowska, Aleksandra

doi:10.1111/cote.12300

Cited by 6 publications

(4 citation statements)

References 41 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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“…The most effective photoinitiators of TMPTA polymerization are compounds containing electron-withdrawing substituents (DBPh4–DBPh7) and heavy atoms (DBPh8 and DBPh9). When designing the structures of these compounds, we took into account previous research results on the heavy-atom effect based on the skeleton of pyridopyrazinoindole, pyrazolo[3,4-b]quinoxaline [ 72 ], pyrazoloquinoline [ 73 ], quinolineimidazopyridine [ 74 ], styrylbenzothiazole [ 75 ], naphthoylenebenzimidazolone [ 76 ], and quinoxaline[2,3-b]quinoxaline [ 77 ]. Chlorine, bromine, or iodine atoms are also often present in the structure of dyes used in photochemistry, e.g., Rose Bengal [ 78 ], RBAX [ 79 ], or 3-hydroxy-6-fluorone derivatives [ 80 ].…”

Section: Resultsmentioning

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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“…The raw materials, DANQ and TABQ, were prepared according to the same reported method (Scheme S1) − and characterized by FTIR (Figure S1) and NMR spectra (Figure S2 and S3) to confirm their successful synthesis. The two steps of reactions, i.e., quinone–amino condensation to form the molecular skeleton , and an oxidation reaction to form the o -quinone groups, , were inspired separately by the literature and combined together for the first time. Especially, we modified the precursor of the second step of oxidation by HNO 3 from the reported pyridinium phenolate , to a single-hydroxyl-substituted moiety (HDABTDO and DHTADBPDO), which was an efficient, low-cost, and environmentally friendly approach to acquire o -quinone groups in comparison to previously reported methods employing NaIO 4 , RuCl 3 , Na 2 Cr 2 O 7 , and Ce(NH 4 ) 2 (NO 3 ) 6 as the oxidant.…”

Section: Resultsmentioning

confidence: 99%

“…The two steps of reactions, i.e., quinone–amino condensation to form the molecular skeleton , and an oxidation reaction to form the o -quinone groups, , were inspired separately by the literature and combined together for the first time. Especially, we modified the precursor of the second step of oxidation by HNO 3 from the reported pyridinium phenolate , to a single-hydroxyl-substituted moiety (HDABTDO and DHTADBPDO), which was an efficient, low-cost, and environmentally friendly approach to acquire o -quinone groups in comparison to previously reported methods employing NaIO 4 , RuCl 3 , Na 2 Cr 2 O 7 , and Ce(NH 4 ) 2 (NO 3 ) 6 as the oxidant. Moreover, since the first step resulted in a high yield of the intermediate product (90% for HDABTDO or 86% for DHTADBPDO) and adopted the same solvent of HOAc as for the second step, it is highly possible to further simplify the procedures to a one-pot synthesis in the future.…”

Section: Resultsmentioning

confidence: 99%

Constructing Extended π-Conjugated Molecules with o-Quinone Groups as High-Energy Organic Cathode Materials

Chen

Wang

Cai

et al. 2022

ACS Appl. Mater. Interfaces

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Although organic cathode materials with sustainability and structural designability have great potential for rechargeable lithium batteries, the dissolution issue presents a huge challenge to meet the demands of cycling stability and energy density simultaneously. Herein, we have designed and successfully synthesized two novel small-molecule organic cathode materials (SMOCMs) by the same innovative route, namely 7,14-diazabenzo[a]tetracene-5,6,8,13-tetraone (DABTTO) and 7,9,16,18-tetraazadibenzo[a,l]pentacene-5,6,8,14,15,17-hexaone (TADBPHO). The integrated p-quinone, o-quinone, and pyrazine groups provide these SMOCMs with attractive theoretical capacities of 473 and 568 mAh g–1 based on 6- and 10-electron reactions, respectively, which were almost fully utilized within 0.8–3.8 V vs Li+/Li. The extended aromatic nucleus of TADBPHO makes it much less soluble than DABTTO and thus able to achieve the highest level of cycling stability (66% @ 500th cycle) for SMOCMs in addition to the exceptional energy density (364 mAh g–1 × 2.56 V = 932 Wh kg–1) within 1.5–3.8 V. In addition to the excellent electrochemical performance, the redox reaction and capacity fading mechanisms have been also investigated in detail. The novel approach to construct extended π-conjugated molecules with o-quinone groups is enlightening for the development of high-energy and stable OCMs for future efficient and sustainable energy storage devices.

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Synthesis and photochemical reaction of benzo[a]quinoxalino[2,3‐c]phenazine dyes

Cited by 6 publications

References 41 publications

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

Acenaphthoquinoxaline Derivatives as Dental Photoinitiators of Acrylates Polymerization

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

Constructing Extended π-Conjugated Molecules with o-Quinone Groups as High-Energy Organic Cathode Materials

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