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

Jin, Ming; Yu, Man; Zhang, Yuan; Wan, Decheng; Pu, Hongting

doi:10.1002/pola.28053

Cited by 23 publications

(16 citation statements)

References 50 publications

(73 reference statements)

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“…Such natural dyes exhibit great potential to act as nontoxic photoinitiators for the fabrication of biocompatible polymeric materials . After the absorption of suitable light, natural dyes are promoted to excited states and can then interact with additives through electron (or energy) transfer reactions to yield active species (e.g., cations or radicals) to initiate photopolymerization reactions . The relevant reactivity between natural dyes and additives is strongly related to their photochemical properties.…”

Section: Introductionmentioning

confidence: 99%

Multihydroxy‐Anthraquinone Derivatives as Free Radical and Cationic Photoinitiators of Various Photopolymerizations under Green LED

Zhang

Hill

Lalevée

et al. 2018

Macromol. Rapid Commun.

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Multihydroxy-anthraquinone derivatives [i.e., 1,2,4-trihydroxyanthraquinone (124-THAQ), 1,2,7-trihydroxyanthraquinone (127-THAQ), and 1,2,5,8-tetrahydroxyanthraquinone (1258-THAQ)] can interact with various additives [e.g., iodonium salt, tertiary amine, N-vinylcarbazole, and 2-(4-methoxystyryl)-4,6-bis(trichloromethyl)-1,3,5-triazine] under household green LED irradiation to generate active species (cations and radicals). The relevant photochemical mechanism is investigated using quantum chemistry, fluorescence, cyclic voltammetry, laser flash photolysis, steady state photolysis, and electron spin resonance spin-trapping techniques. Furthermore, the multihydroxy-anthraquinone derivative-based photoinitiating systems are capable of initiating cationic photopolymerization of epoxides or divinyl ethers under green LED, and the relevant photoinitiation ability is consistent with the photochemical reactivity (i.e., 124-THAQ-based photoinitiating system exhibits highest reactivity and photoinitiation ability). More interestingly, multihydroxy-anthraquinone derivative-based photoinitiating systems can initiate free radical crosslinking or controlled (i.e., reversible addition-fragmentation chain transfer) photopolymerization of methacrylates under green LED. It reveals that multihydroxy-anthraquinone derivatives can be used as versatile photoinitiators for various types of photopolymerization reactions.

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Section: Introductionmentioning

confidence: 99%

Multihydroxy‐Anthraquinone Derivatives as Free Radical and Cationic Photoinitiators of Various Photopolymerizations under Green LED

Zhang

Hill

Lalevée

et al. 2018

Macromol. Rapid Commun.

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“…The aerated film was irradiated at different LED sources (385 and 405 nm). The evolution of the double‐bond (CC) content of TMPTA were continuously followed by RT‐FTIR at approximately 1,630 cm −1 . The degree of double‐conversion (DC) of the function groups could be calculated by measuring the peak area at each time of the reaction and determined by the following Equation .…”

Section: Methodsmentioning

confidence: 99%

Bicarbazole‐based oxalates as photoinitiating systems for photopolymerization under UV–Vis LEDs

Zhou

Jin

Malval

et al. 2020

Journal of Polymer Science

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Photoinitiators are critical to initiate chain reactions in photopolymerization. For such applications, the absorption of photoinitiator must be compatible with the emission of light sources and enables the fast manufacturing of threedimensional network or structures. Light-emitting diode (LED) is a new kind of energy-saving and environmental protection light source, exhibiting a substantial response in the near UV and visible range to replace the traditional mercury lamp and other light sources in photopolymerization. Here, we introduce methyl oxalate into bicarbazole chromophore (BiCz). By variation of the single or double substituents in the BiCz, we demonstrate that the absorption spectra can be adjusted and redshift to visible range and show good absorption in the near UV and visible range (365-475 nm). We explore their photochemistry based on experimental results and theoretical calculations and the mechanism of photoreactions have been verified. The super photostability by themselves and good hydrogen abstraction ability from amine co-initiator make them as excellent near UV and visible light active photoinitiators. Critically, the photoinitiation of the free-radical polymerization of acrylate monomers with low content (0.1% concentration) upon LED irradiation at 365-475 nm, exhibits excellent application potential in light curing and other fields. K E Y W O R D S photoinitiators, free-radical polymerization, UV-visible LEDs, high efficiency

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“…The synthetic route of PAGs is shown in Scheme , and the precursor PI‐Ben and PI‐Flu were prepared in the previous article …”

Section: Methodsmentioning

confidence: 99%

D‐π‐a‐type oxime sulfonate photoacid generators for cationic polymerization under UV–visible LED irradiation

Jin

Zhou

et al. 2018

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

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Four D-p-A-type nonionic oxime sulfonate photoacid generators (PAGs) have been designed and synthesized for use in light-emitting diode (LED) excitable cationic photoinitiators, in which N,N-diphenylamino was used as electron donor with trifluoroacetophenone-based oxime sulfonates (trifluoromethanoesulfonate and p-toluenesulfonate) as electron acceptor and substituted fluorene and biphenyl groups as the p-conjugated systems. PAG-Ben-Tol (with biphenyl and p-toluenesulfonate) and PAG-Flu-Tol (with fluorene and p-toluenesulfonate) showed high quantum yields of photoacid generation (0.33-0.50) and very good thermal stability (over 250 8C). The absorbance spectra of these PAGs were consistent with the emission spectra of commercially gained UV-visible LED light sources.The potential of these PAGs for cationic photoinitiators was tested in two cationic monomer systems. These PAGs needed low light intensity and low concentration for photopolymerization with high conversions of monomer, for example, over 80%, gained at 3.0 mW cm 22 from 365 to 470 nm LEDs. The photochemical mechanisms of these PAGs are comprehensively investigated and discussed in detail.

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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

Cited by 23 publications

References 50 publications

Multihydroxy‐Anthraquinone Derivatives as Free Radical and Cationic Photoinitiators of Various Photopolymerizations under Green LED

Multihydroxy‐Anthraquinone Derivatives as Free Radical and Cationic Photoinitiators of Various Photopolymerizations under Green LED

Bicarbazole‐based oxalates as photoinitiating systems for photopolymerization under UV–Vis LEDs

D‐π‐a‐type oxime sulfonate photoacid generators for cationic polymerization under UV–visible LED irradiation

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