Synthesis and photochemical transformations of an anthracene containing methacrylic copolymer

Bratschkov, Christo; Karpuzova, Pluma; Müllen, Kläus; Klapper, Markus; Schopov, Ivan

doi:10.1007/s002890170041

Cited by 22 publications

(21 citation statements)

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“…The presence of the PEG chain clearly caused a reduction in dimerization and de‐dimerization efficiency, consistent with past literature which indicates that bound groups can lower anthracene photoreactivity likely due to steric hindrance 22. However, the PEG chains are crucial to allow anthracene to solubilize in aqueous medium and to give mobility to the anthracene to allow photoreactions after grafting to the backbone of bulk polymers 36. Importantly, the photoreactivity of the PEG–anthracene is at acceptable levels and showed the ability to undergo significant dimerization and de‐dimerization.…”

Section: Resultssupporting

confidence: 88%

“…Attempts at the modification of polymers with anthracene have mainly focused on direct alteration of hydrophobic polymers. Modification of polystyrene,33, 34 methacrylate,35–37 and polyoxazoline38 with anthracene have demonstrated some photoresponsiveness. The most promising approach involves direct modification of star‐PEG with anthracene to create thin sheets with hydrophobic aggregation that showed photoresponsiveness16 but this was not pursued and limited to PEG polymers.…”

Section: Introductionmentioning

confidence: 99%

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Generic, Anthracene‐Based Hydrogel Crosslinkers for Photo‐controllable Drug Delivery

Wells

Brook

Sheardown

2011

Macromolecular Bioscience

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Light-responsive polymers with controllable, reversible crosslink mechanisms have the potential to create unique biomaterials with stimulus-controlled swelling, degradation and diffusion properties useful in tissue engineering and drug delivery applications. Generic photodimerizing polyethylene glycol-anthracene macromolecules that may be grafted to various polymers to effectively control their crosslinking via a photodimerization mechanism have been developed. These generic crosslinkers were shown to effectively introduce photoresponsive properties into hyaluronate and alginate as model hydrophilic polymers. In vitro testing using human corneal epithelial cells was used to demonstrate cytocompatibility of the resulting photogels. The effective crosslinking density of the photogels could be increased resulting in a decrease in the release rate of small and large molecules from the photogels following exposure to 365 nm light. This tuneable crosslinking has the potential to manipulate the delivery rates of therapeutics resulting in control over treatment profiles and may lend itself to various applications, which may benefit from light induced changes in crosslinking.

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Section: Resultssupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Generic, Anthracene‐Based Hydrogel Crosslinkers for Photo‐controllable Drug Delivery

Wells

Brook

Sheardown

2011

Macromolecular Bioscience

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“…Photodimerization is a well‐known major photochemical reaction of anthracene. However, formation of endoperoxide is the only photoreaction that occurs in the presence of oxygen . As irradiation of the polymer film was carried out in the presence of oxygen, formation of endoperoxide seemed to be the only photochemical process to bleach the anthracene groups.…”

Section: Resultsmentioning

confidence: 99%

Formation of Various Bicolor Fluorescent Micropatterns on a Single Polymer Film Based on Concurrent Photobleaching and Photobase Generation

Chae

Kim

2015

Macromol. Rapid Commun.

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Various bicolored fluorescent micropatterns are fabricated on a single polymer film by concurrent photobleaching and a photobase generation process. A polymer, bearing anthracene and oxime-urethane groups, is dyed with rhodamine B isothiocyanate after irradiation with 310-nm UV light. The photochemical reaction of the polymer is monitored by UV, IR absorption, and fluorescence emission spectroscopy. Differently colored fluorescent micropatterns are obtained by selectively exciting each dye moiety. Various bicolored fluorescent micropatterns are observed through varying the excitation wavelength and observation wavelength ranges using a confocal microscope. This bicolored fluorescence patterning method will be useful to apply in photonic/electronic devices.

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“…[4,[10][11][12] A great number of studies were performed on this photoinduced dimerization reaction, revealing a mechanism based on a [4π + 4π] cycloaddition of the central ring of the anthracene π-system. [13][14][15][16][17][18][19][20][21][22] It is important to know that the photodimerization reaction takes place purely in the absolute absence of oxygen, otherwise the formation of endoperoxides occurs. [23,24] Thioxanthone-anthracene (TX-A) (Chart 1) was previously synthesized and its photoinitiation efficiency and mechanisms were investigated.…”

Section: Introductionmentioning

confidence: 99%

Photodimerization of thioxanthone–anthracene: formation of monochromophoric Type II initiator

Balta

Arsu

2016

Designed Monomers and Polymers

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Thioxanthone-anthracene (TX-A) was previously synthesized and used as an initiator for the polymerization of acrylates and methacrylates in air atmosphere. Photodimerization of TX-A was carried out in benzene under light irradiation of >350 nm, and dimer (diTX-A) formation was followed by UV-vis, fluorescence and phosphorescence spectroscopy. The conjugation of anthracene was destroyed after dimerization, and the thioxanthone group was left behind. Therefore, the typical thioxanthone absorption spectrum was seen at 380 nm. TX-A itself does not have phosphorescence emission; however, diTX-A displayed phosphorescence emission spectrum similar to thioxanthone. IR and 1 H NMR spectrophotometric techniques also helped to determine the structure of diTX-A. Furthermore, photopolymerization of methyl methacrylate (MMA) in the presence of dimer (diTX-A) was another proof of the photodimerization of TX-A. diTX-A initiated polymerization of MMA as good as thioxanthone in the nitrogen atmosphere and displayed typical Type II initiator behaviour.

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Synthesis and photochemical transformations of an anthracene containing methacrylic copolymer

Cited by 22 publications

References 0 publications

Generic, Anthracene‐Based Hydrogel Crosslinkers for Photo‐controllable Drug Delivery

Generic, Anthracene‐Based Hydrogel Crosslinkers for Photo‐controllable Drug Delivery

Formation of Various Bicolor Fluorescent Micropatterns on a Single Polymer Film Based on Concurrent Photobleaching and Photobase Generation

Photodimerization of thioxanthone–anthracene: formation of monochromophoric Type II initiator

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