Functionalised PEGs with photo-dimerisable, anthracenyl end-groups: New UV-curable materials for use in inkjet formulations

Godleman, Jessica; Babra, Tahkur S.; Afsar, Ashfaq; Kyriacou, Andrew; Thompson, Mark; Harries, Josephine L.; Colquhoun, Howard M.; Hayes, Wayne

doi:10.1016/j.porgcoat.2020.106105

Cited by 5 publications

(7 citation statements)

References 45 publications

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“…Ma et al described the mechanoluminescent properties of a tri‐arm polyurethane that was end‐capped with anthracene units [91] . Hayes et al reported a UV light‐curable 3‐arm PEG grafted with anthracene moieties as end groups (Figure 20, structure 6) that showed potential use in inkjet formulations [92] …”

Section: [4+4] Photocycloaddition Of Anthracene‐containing Polymersmentioning

confidence: 99%

“…[89] 3-arm PEG grafted with anthracene moieties (6), M n = 1600 g/mol. [92] Hyperbranched polyglycerols (M n = 8200 g/mol) functionalized with anthracene groups (7). Reprinted with permission.…”

Section: Star Polymersmentioning

confidence: 99%

“…[91] Hayes et al reported a UV light-curable 3-arm PEG grafted with anthracene moieties as end groups (Figure 20, structure 6) that showed potential use in inkjet formulations. [92] Liu and co-workers reported a phototunable supramolecular network comprised of γ-cyclodextrin (γ-CD), 4-(anthracen-2yl)pyridine-2,6-dicarboxylic acid (APDA) and Eu(III) in aqueous solution. [93] The supramolecular network assembled into a branched star-shape polymer via complexation of γ-CD and anthryl groups of APDA (1 : 2) and coordination between Eu(III) and carboxylic acid moieties in 1 : 3 ratio.…”

Section: Star Polymersmentioning

confidence: 99%

“…Poly(methacrylic acid) modified with anthracene (5) [89]. 3-arm PEG grafted with anthracene moieties (6), M n = 1600 g/mol [92]. Hyperbranched polyglycerols (M n = 8200 g/mol) functionalized with anthracene groups (7).…”

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confidence: 99%

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Photo‐Controlled [4+4] Cycloaddition of Anthryl‐Polymer Systems: A Versatile Approach to Fabricate Functional Materials

Paderes

Diaz

Pagtalunan

et al. 2022

Chemistry An Asian Journal

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The reversible photo‐induced [4+4] cycloaddition reaction of anthracene enables multiple cycles of dimerization and scission, allowing phototunable linkage of molecular fragments for the synthesis of polymer scaffolds. New functional materials ranging from hydrogels to shape‐memory polymers were designed from anthryl‐polymer systems because of their diverse photochemical reactivity and responsiveness. Light as an external stimulus allows for the remote and precise spatiotemporal control of materials without the need for additional reagents. Depending on how the photoreactive anthracene moieties were introduced, the interaction of anthryl‐polymer systems with light results in various processes such as polymerization, cyclization, and cross‐linking. Structural modifications of anthracene derivatives could shift their absorption from the ultraviolet to the visible light region, widening their range of applications including biologically relevant studies. These applications are further diversified and enhanced by the reversibility of the dimerization reaction using light and heat as stimuli. In this review, current developments in the synthesis and photodimerization of anthracene‐containing polymers and their emerging applications in the fabrication of new materials are discussed.

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Section: [4+4] Photocycloaddition Of Anthracene‐containing Polymersmentioning

confidence: 99%

Section: Star Polymersmentioning

confidence: 99%

Section: Star Polymersmentioning

confidence: 99%

mentioning

confidence: 99%

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Photo‐Controlled [4+4] Cycloaddition of Anthryl‐Polymer Systems: A Versatile Approach to Fabricate Functional Materials

Paderes

Diaz

Pagtalunan

et al. 2022

Chemistry An Asian Journal

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“…Light‐curing technology refers to the process of changing materials from small molecules to polymers under the irradiation of light sources. Light‐curing technology has been widely used in inks, coatings, pressure‐sensitive adhesives, food packaging, dental resins, and biological materials fields due to energy saving, high efficiency, and almost no volatile organic compounds 1–10 . Typical light sources are medium and high‐pressure mercury lamps, which possesses some disadvantages including high energy consumption and environmental pollution, they would be replaced by ultraviolet‐light emitting diode (UV‐LED) 11–14 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of acyldiphenylphosphine oxides photoinitiators carrying triphenylamine or pyrene group for free radical photopolymerization

Luo

2023

J of Applied Polymer Sci

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Two new photoinitiators of acyldiphenylphosphine oxides carrying triphenylamine (NHPO) or pyrene group (BHPO) were designed and synthesized with diphenylphosphine oxide reacting with 4‐(diphenylamino) benzaldehyde or 1‐pyrenecarboxaldehyde. The solubility of NHPO is about 13.7 wt% in TMPTA, which is higher than that of (2,4,6‐trimethylbenzoyl) diphenylphosphine oxide (TPO) (about 12.5 wt%). The UV–Vis spectrum of NHPO and BHPO revealed that their maximum absorption wavelengths have redshifted to 397 and 419 nm, respectively, with a molar extinction coefficient of around 19,057 and 24,257 M−1 cm−1, suggesting that they are likely to be effective photoinitiators when exposed to light from LEDs. According to real‐time Fourier transform infrared spectroscopies, the degree of double bond conversion of NHPO reached 65%, which was higher than that of TPO (about 45%), showing that NHPO had substantially better photoinitiated properties than TPO. Using steady‐state photolysis and electron spin resonance spin‐trapping studies, the photocuring mechanism was examined, and it was discovered that the NHPO and BHPO had produced two free radicals. Additionally, NHPO exhibited superior biocompatibility performance as demonstrated by cytotoxicity assays and had a low migration rate of only 0.23%, as determined by migration. As a result, NHPO might be utilized in coatings for food packaging.

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An effective route to the additive manufacturing of a mechanically gradient supramolecular polymer nanocomposite structure

Salimi,

Graham,

et al. 2024

Journal of the Mechanical Behavior of Biomedical Materials

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Functionalised PEGs with photo-dimerisable, anthracenyl end-groups: New UV-curable materials for use in inkjet formulations

Cited by 5 publications

References 45 publications

Photo‐Controlled [4+4] Cycloaddition of Anthryl‐Polymer Systems: A Versatile Approach to Fabricate Functional Materials

Photo‐Controlled [4+4] Cycloaddition of Anthryl‐Polymer Systems: A Versatile Approach to Fabricate Functional Materials

Synthesis and properties of acyldiphenylphosphine oxides photoinitiators carrying triphenylamine or pyrene group for free radical photopolymerization

An effective route to the additive manufacturing of a mechanically gradient supramolecular polymer nanocomposite structure

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