A benzophenone‐naphthalimide derivative as versatile photoinitiator of polymerization under near <scp>UV</scp> and visible lights

Zhang, Jing; Zivic, Nicolas; Dumur, Frédéric; Xiao, Pu; Graff, Bernadette; Gigmès, Didier; Fouassier, Jean Pierre; Lalevée, Jacques

doi:10.1002/pola.27451

Cited by 102 publications

(74 citation statements)

References 59 publications

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“…6(a)]. 8,39,50 When mixing with Iod, the key step is the photoinduced electron transfer (PET) process between the PI/Iod photoredox pair. The PET from the excited dye ( 1 PI) to iodonium (Ph 2 I 1 ) leads to the dye radical cation (PI •1 ) and neutral radical (Ph • ), as shown in the ESR-ST curve in Figure 6(b).…”

Section: Excited States Reactions Of Pis Themselves and With Pis And mentioning

confidence: 99%

“…These results are attributed to an oxidation of PI-Ben by iodonium in the PI-Ben/Iod couple as observed in the reported PISs. 8 The possible photodecomposition mechanism of the substituted acetophenone (type I) is presented in reactions 1-2 (r 1 -r 2 ). 49 The formation of radicals in (r 2 ) is also well-supported by ESR-ST experiments when PIs themselves are photodecomposited and the photogenerated radicals are trapped by PBN in tert-butylbenene under Argon [ Fig.…”

Section: Excited States Reactions Of Pis Themselves and With Pis And mentioning

confidence: 99%

“…7 UV and visible lightemitting diodes (LEDs) are new light sources with advantages including soft irradiation, lack of harmful UV, higheroperating efficiency, and low cost. [8][9][10][11][12][13] However, most reported and commercial PIs exhibit less-than-perfect performance upon LED irradiation because they have a maximum absorbance below 365 nm where the most common and cost-effective UV/LED lamps irradiate. 14 In the reported PIs, substituted ketones (e.g., the well-known 2,2-dimethoxy-2-phenylacetophenone (DMPA), 15,16 benzophenone (BP), [17][18][19][20][21] or thioxanthone (TX) [22][23][24][25][26] ) can work as cleavable (Type I) or uncleavable (Type II) PIs, and their photogenerated radicals is used for universal application in free-radical polymerization (FRP), free-radical-promoted cationic photopolymerization, or in cationic polymerization (CP) (as photosensitizers).…”

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confidence: 98%

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2,2,2-trifluoroacetophenone-based D-π-A type photoinitiators for radical and cationic photopolymerizations under near-UV and visible LEDs

Jin

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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Two D-p-A-type 2,2,2-trifluoroacetophenone derivatives, namely, 4'-(4-( N,N-diphenyl)amino-phenyl)-phenyl-2,2,2-trifluoroacetophenone (PI-Ben) and 4'-(4-(7-(N,N-diphenylamino)-9,9-dimethyl-9H-fluoren-2-yl)-phenyl-2,2,2-trifluoroacetophenone (PI-Flu), are developed as high-performance photoinitiators combined with an amine or an iodonium salt for both the free-radical polymerization of acrylates and the cationic polymerization of epoxides and vinyl ether upon exposure to near-UV and visible lightemitting diodes (LEDs; e.g., 365, 385, 405, and 450 nm). The photochemical mechanisms are investigated by UV-Vis spectra, molecular-orbital calculations, fluorescence, cyclic voltammetry, photolysis, and electron-spin-resonance spin-trapping techniques. Compared with 2,2,2-trifluoroacetophenone, both photoinitiators exhibit larger redshift of the absorption spectra and higher molar-extinction coefficients. PI-Ben and PI-Flu themselves can produce free radicals to initiate the polymerization of acrylate without any added hydrogen donor. These novel D-p-A type trifluoroacetophenone-based photoinitiating systems exhibit good efficiencies (acrylate conversion 5 48%-66%; epoxide conversion 5 85%-95%; LEDs at 365-450 nm exposure) even in low-concentration initiators (0.5%, w/w) and very low curing light intensities (1-2 mW cm 22 ).

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Section: Excited States Reactions Of Pis Themselves and With Pis And mentioning

confidence: 99%

Section: Excited States Reactions Of Pis Themselves and With Pis And mentioning

confidence: 99%

mentioning

confidence: 98%

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2,2,2-trifluoroacetophenone-based D-π-A type photoinitiators for radical and cationic photopolymerizations under near-UV and visible LEDs

Jin

Zhang

et al. 2016

J. Polym. Sci. Part A: Polym. Chem.

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“…With all these data it is possible to plot a graph of Degree Conversion vs. Time. [29][30][31][32][33][34][35][36][37][38][39][40][41] …”

Section: Mid Infrared Spectroscopy (Mir)mentioning

confidence: 99%

Synthesis, thermal studies and conversion degree of dimethacrylate polymers using new non-toxic coinitiators

Alarcon¹,

Holanda²,

Rinaldo³

et al. 2017

Quim. Nova

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The aim of this paper is to replace toxic coinitiators (tertiary amines) by non-toxic compounds such as glycerol and inositol (polyalcohol) in dimethacrylate resins. For this purpose, mid infrared spectroscopy (MIR) was used to calculate the monomers' degree of conversion (%DC); as well as simultaneous Thermogravimetric Analysis -Differential Thermal Analysis (TGA-DTA) and Differential Scanning Calorimetry (DSC) were conducted to evaluate thermal stability, degradation steps, and thermal events. The use of different initiator systems did not modify the thermal events or the thermal stability of each of the dimethacrylate resins. Results show a substitution of system 2 (toxicity) by system 3 (low toxicity), which had a good conversion velocity and total conversion in some monomers, is plausible.

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“…In the last decade many papers have described the synthesis of initiators. Only thioxanthone [3][4][5][6][7][8][9], benzophenone [10][11][12][13][14][15][16], erythrosine B [17], and, more recently, naphthoquinone [18] and benz[cd]indol-2(1H)-one [19] linked with appropriate groups have been applied as chromophores to obtain one-component initiator systems. There are two different ways to create initiators sensitive to visible radiation.…”

Section: Introductionmentioning

confidence: 99%

Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

Strzelczyk

2017

Coloration Technology

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The appropriate substituents have been added to a 7H-benzimidazo[2,1-a]benz [de]isoquinolin-7-one skeleton in order to obtain a one-component initiator system. The absorption, fluorescence, and electrochemical properties of these naphthoylenebenzimidazolone dyes and their usefulness as visible light initiators of free radical polymerisation of trimethylolpropane triacrylate were examined. The initiation efficiency of these dyes was compared with that of the parent 7H-benzimidazo[2,1-a]benz[de]isoquinolin-7-one in the presence of a coinitiator. Results show that these bifunctional dyes are able to initiate polymerisation without an additional coinitiator. Photopolymerisation studies and the relationship between the rate of polymerisation and the free energy change for electron transfer revealed that, depending on the concentration, initiating radicals are generated via intra-and intermolecular electron transfer.

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A benzophenone‐naphthalimide derivative as versatile photoinitiator of polymerization under near UV and visible lights

Cited by 102 publications

References 59 publications

2,2,2-trifluoroacetophenone-based D-π-A type photoinitiators for radical and cationic photopolymerizations under near-UV and visible LEDs

2,2,2-trifluoroacetophenone-based D-π-A type photoinitiators for radical and cationic photopolymerizations under near-UV and visible LEDs

Synthesis, thermal studies and conversion degree of dimethacrylate polymers using new non-toxic coinitiators

Naphthoylenebenzimidazolone dyes as one‐component photoinitiators

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