Dyes based on the 6,7‐dichloro‐5,8‐quinolinedione skeleton as new type <scp>II</scp> photoinitiators for radical polymerisation

Orzeł, Agnieszka; Podemska, Karolina; Strzelczyk, Rafał; Kolińska, Jolanta; Sokołowska, Jolanta

doi:10.1111/cote.12083

Cited by 11 publications

(7 citation statements)

References 23 publications

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“…In the early visible-light-absorbing initiator systems (Scheme 1), an adequate dye operates as the primary absorber, and an appropriate hydrogen donor (DH) or electron donor/acceptor (Co), after photoinduced electron transfer or hydrogen transfer, yields radicals that initiate polymerisation. Many different compounds have been used as the coinitiator (electron donor/acceptor [3]) or hydrogen donor (acetals [4], alcohols [5], amines [6], benzaldehyde [7], benzoxazines [8], ethers [9], poly(ethylene oxide) [10], thiols [11][12][13][14]). Recently, several silanes, germanes, and borane complexes [15][16][17][18] have been proposed as hydrogen donors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Strzelczyk

Michalski

2016

Coloration Technology

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Several potential initiators based on benz [cd]indol-2(1H)-one dye have been synthesised and evaluated in the radical polymerisation of a system containing trimethylolpropane triacrylate under visible light. Absorption, fluorescence, and phosphorescence spectra and the electrochemical properties of these novel dyes were determined. Owing to the presence of an appropriate hydrogen donor group in their structure, these photoinitiators do not need an extra coinitiator to initiate the polymerisation process. During photopolymerisation they act both as a triplet sensitiser and as a hydrogen donor. The relationship between the polymerisation rate and the triplet-excited-state reduction potential suggests that initiating radicals are formed from the triplet state via hydrogen transfer. This mechanism is supported by density functional theory calculations. 8-Bromo-6-[(2-sulphanylethyl)sulphanyl]benzo[cd]indol-2(1H)-one and 8-bromo-6-sulphanylbenz[cd]indol-2(1H)-one may be applied as visible-light initiators of free radical polymerisation to obtain a low-molecular-weight polymer.

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Section: Introductionmentioning

confidence: 99%

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Strzelczyk

Michalski

2016

Coloration Technology

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“…We have attempted to test phenazine derivatives as photosensitizers in radical polymerization, as new dye structures are still being sought because of the high demands placed on photoinitiators in modern applications such as dental filling materials, reprography (photoresists, printing plates, integrated circuits), laser-induced 3D curing, holographic recordings, and nanoscale micromechanics. Modifications of the photosensitizer structure were carried out by introducing heavy atoms and electron-donating or electron-withdrawing substituents to various heterocyclic rings [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 ] or by the preparation of new chemical skeletons. Our strategy for synthesis followed the modification of phenazine structure by increasing either nitrogen atoms to 3 or 4 in the dye molecule or aromatic rings in the angular and/or linear positions.…”

Section: Introductionmentioning

confidence: 99%

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

2021

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A series of dyes based on the phenazine skeleton were synthesized. They differed in the number of conjugated double bonds, the arrangement of aromatic rings (linear and/or angular system), as well as the number and position of nitrogen atoms in the molecule. These compounds were investigated as potential singlet oxygen sensitizers and visible light absorbers in dye photoinitiating systems for radical polymerization. The quantum yield of the singlet oxygen formation was determined by the comparative method based on the 1H NMR spectra recorded for the tested dyes in the presence of 2,3-diphenyl-p-dioxene before and after irradiation. The quantum yield of the triplet state formation was estimated based on the transient absorption spectra recorded using the nanosecond flash photolysis technique. The effectiveness of the dye photoinitiating system was characterized by the initial rate of trimethylolpropane triacrylate (TMPTA) polymerization. In the investigated photoinitiating systems, the sensitizer was an electron acceptor, whereas the co-initiator was an electron donor. The effectiveness of TMPTA photoinitiated polymerization clearly depended on the arrangement of aromatic rings and the number of nitrogen atoms in the modified phenazine structure as well as the quantum yield of the triplet state formation of the photosensitizer in the visible light region.

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“…ref. [1k],, and the particular use of the LED technology outlined in a recent review . In CP and FRPCP, two‐ and three‐component PISs are currently used (see below).…”

Section: Introductionmentioning

confidence: 99%

Cationic Photoinitiators for Near UV and Visible LEDs: A Particular Insight into One‐Component Systems

Zhang

Xiao

Dietlin

et al. 2016

Macro Chemistry & Physics

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The observed development of one‐component photoinitiators of cationic polymerization reactions in the last forty years is briefly described. Cationic photoinitiators can usually be activated by short wavelengths (<300 nm) and relatively hard conditions (high intensity). The search for cheaper and safer light sources has led to the use of Light Emitting Diodes (LEDs). In this review, a special emphasis is provided on the most recent and promising cationic initiators operating under near UV and visible LEDs. Ferrocenium salts exhibit the broadest visible light absorption and are probably, from this point of view, the most versatile near UV and visible light cationic initiators. Excellent photoinitiation performance has been found with the ferrocenium salts as one‐component initiators, and the effect of ferrocenium salts based multi‐component photoinitiating systems on the relevant photoinitiation performance has also been investigated.

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Dyes based on the 6,7‐dichloro‐5,8‐quinolinedione skeleton as new type II photoinitiators for radical polymerisation

Cited by 11 publications

References 23 publications

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

Synthesis and application of dyes derived from benz[cd]indol‐2(1H)‐one as visible‐light‐absorbing polymerisation photoinitiators

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

Cationic Photoinitiators for Near UV and Visible LEDs: A Particular Insight into One‐Component Systems

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