Recent advances on push–pull organic dyes as visible light photoinitiators of polymerization

Pigot, Corentin; Noirbent, Guillaume; Brunel, Damien; Dumur, Frédéric

doi:10.1016/j.eurpolymj.2020.109797

Cited by 83 publications

(59 citation statements)

References 238 publications

(202 reference statements)

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“…In recent decades, push-pull dyes have attracted a lot of attention due to their numerous applications ranging from non-linear optics (NLO) [1][2] to organic photovoltaics (OPV), [3][4] organic field effect transistors (OFET), [5] organic light emitting diodes (OLED) [6] and polymerization photoinitiators. [7][8][9][10][11][12] Typically, push-pull dyes are molecules comprising an electron donor and an electron acceptor connected by mean of a π -conjugated and planar system. [13][14] This configuration results in a significant electron delocalization from the donor to the acceptor facilitated by the π-conjugated spacer.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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A series of chromophores was designed and synthesized using 2-(3-cyano-4,5,5-trimethylfuran-2 (5H) -ylidene) malononitrile (TCF) as the electron acceptor and differing from each other by the use of thirteen different electron donors. The different dyes were characterized for their optical and electrochemical properties and theoretical calculations were also carried out to support the experimental results. By changing the electron donor in the thirteen dyes, chromophores absorbing between 430 nm and 700 nm could be synthesized. Solvatochromism of the different dyes was analyzed in 23 solvents of different polarity and a positive solvatochromism was determined for all chromophores using the semi-empirical solvent polarity scales based on the Kamlet-Taft parameters (π *) or the Catalan parameters (SdP and SPP).

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Section: Introductionmentioning

confidence: 99%

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

et al. 2021

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“…Dye-photosensitized systems are able to initiate free radical photopolymerizations (FRP) and cationic photopolymerizations (CP) and display a lively interest under LEDs irradiation 16,17 . In the excited state, organic dyes can interact with additives to generate active species capable to induce the polymerization of monomers and oligomers.…”

Section: Introductionmentioning

confidence: 99%

New multifunctional benzophenone-based photoinitiators with high migration stability and their applications in 3D printing

Liu

Brunel

Noirbent

et al. 2021

Mater. Chem. Front.

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“…Researchers showed a number of works regarding the design of new photoinitiators. Currently, it has become a trend to replace traditional ultraviolet (UV) light sources with lower energy consumption (LED light) and/or longer wavelength (visible and near-infrared) exposure light sources [ 23 , 24 ]. This is because of the environmental friendliness, and greater depth of penetration of the latter exposure instrument.…”

Section: Introductionmentioning

confidence: 99%

Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators

Huang

Chen

2021

Polymers

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Three novel visible-light absorbing benzophenone-based hydrogen acceptors (BPD-D, BPDM-D and BPDP-D) were designed on the basis of a donor–benzophenone–donor structural backbone. Mono or diketone units and double diphenylamine electron-donating groups in para-or meta-positions were introduced to comprehend the electronic and structural effects on free radical photopolymerization (FRPP). Such a structural change leads not only to a red-shift of the absorption maxima but strongly enhances their molar extinction coefficients compared to the commercial phototinitiators such as benzophenone (BP) and 4,4′-bis(diethylamino) benzophenone (EMK). In addition, excellent melting points and thermal decomposition temperatures were achieved for those novel compounds. Further, the photochemical reaction behavior was studied by cyclic voltammograms (CV), photolysis and electron spin resonance (ESR) spectroscopy. Finally, benzophenone derivatives in combination with an amine (TEA, triethylamine) as a co-initiator were prepared and initiated the FRPP of trimethylolpropane trimethacrylate (TMPTMA) using a UV lamp as a light source. When used in stoichiometric amounts, the BPDP-D/TEA had the best double bond conversion efficiency among all the compounds studied, and were even superior to the reference compounds of BP/TEA and EMK/TEA. The results and conclusions could provide the fundamental rules applicable for the structural design of benzophenone derivative-based photoinitiators.

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Recent advances on push–pull organic dyes as visible light photoinitiators of polymerization

Cited by 83 publications

References 238 publications

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

Synthesis, optical and electrochemical properties of a series of push-pull dyes based on the 2-(3-cyano-4,5,5-trimethylfuran-2(5H)-ylidene)malononitrile (TCF) acceptor

New multifunctional benzophenone-based photoinitiators with high migration stability and their applications in 3D printing

Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators

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