A blue to red light sensitive photoinitiating systems based on 3,5-di-tert-butyl-o-benzoquinone derivatives for free radical polymerization

Shurygina, M. P.; Zakharina, M. Yu.; Батенькин, М. А.; Конев, А. Н.; Shavyrin, A. S.; Chelnokov, Egor A.; Shushunova, N. Yu.; Arsenyev, Maxim V.; Чесноков, С. А.; Абакумов, Г. А.

doi:10.1016/j.eurpolymj.2020.109573

Cited by 27 publications

(20 citation statements)

References 45 publications

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“…The Cd–O (2.47, 2.39 Å) and Cd–N (2.35, 2.36 Å) distances in [ 2 ·CdI 2 ] 2 and [ 5 ·CdI 2 ] 2 ·2CH 3 CN as well as Hg–O (2.56 Å) and Hg–N (2.50, 2.47 Å) distances in 5 ·HgBr 2 and 5 ·HgI 2 are longer than the sum of the covalent radii of the elements (Cd–O: 2.24 Å; Cd–N: 2.25 Å; Hg–O: 2.23 Å; Hg–N: 2.24) and considerably smaller than the sum of their van der Waals radii (Cd···O, Hg···O: 3.6 Å; Cd···N, Hg···N: 3.7 Å), which indicates a donor–acceptor nature of these bonds. The Zn–O distances (2.08 Å) slightly exceed the sum of covalent radii of corresponding elements (2.07 Å) . These bond lengths are considerably shorter than in 5 ·ZnI 2 and closer to Zn–O distances in zinc o -benzosemiquinonates .…”

Section: Resultsmentioning

confidence: 79%

“…Consequently, they are the best candidates to produce desired molecular complexes with metal halides. As current research has shown, the nearest analogue of 3,6-Q, 3,5-di- tert -butyl- o -benzoquinone (3,5-Q), undergoes reduction immediately under coordination to the metal iodides, despite their potentials barely differing (−0.50 V vs −0.51 V for 3,5-Q and 3,6-Q, respectively). At the same time, being weaker acceptors than o -quinones, unreduced o -iminoquinones coordinate to the metals more willingly, and variation of N -aryl substituents allows expanding the ligands set applicable for imQ·MX n -type complexes formation (where MX n is metal halide).…”

Section: Resultsmentioning

confidence: 99%

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Complexes of Metal Halides with Unreduced o-(Imino)quinones

et al. 2021

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A series of complexes of metal halides with unreduced quinone-type ligands have been synthesized and characterized in detail. The 3,6-di-tert-butyl-obenzoquinone (1) and 4,6-di-tert-butyl-N-aryl-substituted o-iminobenzoquinones (2−5) (aryl is 2,6-dimethylphenyl in 2, 2-methyl-6-ethylphenyl in 3, 2,6-diethylphenyl in 4, and 2,6-diisopropylphenyl in 5) were used to obtain the molecular complexes with metal 12 group halides as well as with indium(III) iodide. The molecular structures of five complexes, bearing an unreduced form of redox-active ligand, have been established by single-crystal X-ray analysis. The spectral data, electrochemical measurements, and DFT calculations indicate the significant transformations of the molecular orbitals of 1−5 upon complexation with Lewis acids. The reduction potentials of o-(imino)quinones in complexes with metal halides shift into the anodic region versus uncoordinated ones. The choice of metal halide allows varying the shift magnitude up to 1.7 V in 2•CdI 2 . The change of the oxidizing ability of the 1−5 upon coordination with Lewis acids enables the oxidation of mercury and ferrocene, infeasible for free ligands.

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Section: Resultsmentioning

confidence: 79%

Section: Resultsmentioning

confidence: 99%

Complexes of Metal Halides with Unreduced o-(Imino)quinones

et al. 2021

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“…[128][129][130] Indeed, cationic polymerization upon green light irradiation is quite difficult, thus a majority of research is based on FRP. 131,132 Many newly developed green light-sensitive dyes based on different chemical structures exhibited outstanding photophysical and photochemical properties which are possible to enhance the photoinitiation abilities of PISs and the polymerization efficiency of FRPs. 133 However, even if many advantages such as a deeper light penetration in the monomers, were evidenced while using green light sources in the photopolymerization, surprisingly, few PISs adapted for these wavelengths have been developed to date, compared to that done for purple or blue/UV light sources at a wavelength of 350-492 nm.…”

Section: Green Light-sensitive Dyesmentioning

confidence: 99%

“…In previous publications, many researches have been focused on green light‐sensitive dyes as photoinitiators for FRP (or cationic polymerization) under green light sources at 492–577 nm, especially at 520 nm 128–130 . Indeed, cationic polymerization upon green light irradiation is quite difficult, thus a majority of research is based on FRP 131,132 . Many newly developed green light‐sensitive dyes based on different chemical structures exhibited outstanding photophysical and photochemical properties which are possible to enhance the photoinitiation abilities of PISs and the polymerization efficiency of FRPs 133 .…”

Section: State Of the Artmentioning

confidence: 99%

Organic dye‐based photoinitiating systems for visible‐light‐induced photopolymerization

Sun

Xiao

Dumur

et al. 2021

Journal of Polymer Science

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Even though many organic dyes have been reported as photoinitiators/photosensitizers for free radical polymerization in the literature, the design and development of novel photoinitiating systems based on organic dyes adaptable for visible light irradiation, for example, 405 nm LED and sunlight still remains challenging. Recently, major achievements in the development of high‐performance photoinitiating systems based on organic dyes as light‐harvesting compounds and their uses as photoinitiators for photopolymerization under visible‐light irradiation have clearly emerged, giving rise to abundant literature. In this review, an overview of the recently synthesized chromophores belonging to various families of organic dyes and used as photoinitiators of polymerization during the 2018–2021 period are presented and classified. Recent works have resulted in the development of new chromophores exhibiting remarkable visible light absorption properties and excellent photoinitiation abilities upon irradiation with LEDs and/or sunlight in free radical photopolymerization processes. These developments notably indicate that sunlight has the advantages of being a cheap, unlimited, broad emission spectrum, and energy‐saving light source capable to be an efficient substitute to artificial light sources. The newly developed dye‐based photoinitiating systems designed to initiate visible‐light‐induced photopolymerization processes are likely to expand the scope of application of photopolymerization in modern sciences and technologies.

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“…Catechol 1 (4,6-di- tert -butyl-1,2-dihydroxybenzaldehyde) was synthesized from 3,5-di- tert -butylcatechol . Variation of the substituents in the sixth position of the spatially shielded catechol/ o -quinone allows us to expand the redox properties of these compounds . Compound 1 is a convenient structural block for the synthesis of new sterically hindered catecholaldimines. − o -Hydroxy Schiff bases tautomerize via an intramolecular proton transfer and they have potential applications in higher energy radiation detectors and memory storage devices …”

Section: Introductionmentioning

confidence: 99%

Imine-Based Catechols and o-Benzoquinones: Synthesis, Structure, and Features of Redox Behavior

et al. 2020

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Novel sterically hindered catechols of the type 3-(RN=CH)-4,6-DBCatH 2 with iminoalkyl or iminoaryl groups in the third position of the aromatic ring have been synthesized and characterized in detail. The o -benzoquinones 3-(RN=CH)-4,6-DBBQ have been synthesized by the oxidation of the corresponding catechols. The oxidation of methylimino-substituted catechol with K 3 [Fe(CN) 6 ] in alkaline medium leads to the formation of two products: o -quinone and diene–dione, the product of the water addition to the corresponding o -quinone. Some o -benzoquinones react with water or methanol to yield products of water or methanol addition. A prototropic tautomerism is characteristic of catecholaldimines: a quinomethide form is observed in the case of aliphatic amine derivatives, while aryl-substituted catecholaldimines can exist both in the catechol and quinomethide forms in the crystalline state. The formation of dimeric structures motifs is observed in crystals. The electrochemical oxidation of imino-based catechols proceeds via two one-electron processes; the second wave is quasi-reversible, which is unusual for catechols.

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A blue to red light sensitive photoinitiating systems based on 3,5-di-tert-butyl-o-benzoquinone derivatives for free radical polymerization

Cited by 27 publications

References 45 publications

Complexes of Metal Halides with Unreduced o-(Imino)quinones

Complexes of Metal Halides with Unreduced o-(Imino)quinones

Organic dye‐based photoinitiating systems for visible‐light‐induced photopolymerization

Imine-Based Catechols and o-Benzoquinones: Synthesis, Structure, and Features of Redox Behavior

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