Atom-transfer radical homo- and copolymerization of carbazole-substituted styrene and perfluorostyrene

Vaitusionak, Aliaksei A.; Vasilenko, Irina V.; Sych, Galyna; Кашина, А. В.; Simokaitienė, Jūratė; Gražulevičius, Juozas V.; Kostjuk, Sergei V.

doi:10.1016/j.eurpolymj.2020.109843

Cited by 5 publications

(12 citation statements)

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“…Poly( N -isopropylacrylamide) synthesized in the presence of DMP as a RAFT agent in 1,4-dioxane as a solvent is characterized by a close to theoretical number-average molar mass and low dispersity, confirming the reaction proceeding in a controlled fashion (Table ). Homopolymerizations of poly( d , l -lactide) with methacrylate (PLA-MA600) and acrylate (PLA-A500) groups produce polymers with a significantly lower experimentally determined number-average molar mass than the theoretical one, which could be explained by the underestimation of the molar mass measured by conventional SEC for such brush-type polymers. − However, the polydispersities of polymers are rather low, especially those for polymers prepared from PLA-A500, indicating the certain control over polymerization in the case of homopolymerization of macromonomers (Table ).…”

Section: Resultsmentioning

confidence: 99%

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Ksendzov

Nikishau

Зурина

et al. 2022

ACS Appl. Polym. Mater.

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A series of well-defined poly(D,L-lactide) and poly(ε-caprolactone) macromonomers (M n of ∼ 600 and ∼1200 Da) bearing a (meth)acrylate group at one side of the chain and either a hydrophobic nonpolar butyl group or a hydrophilic polar hydroxyl group at the other side of the chain were synthesized via 1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed ring-opening polymerization (ROP) of D,L-lactide and methanesulfonic acidcatalyzed ROP of ε-caprolactone, respectively. Then, a series of well-defined random copolymers (M n of ∼ 30 000 Da, Đ < 1.25) were prepared via reversible addition−fragmentation chain transfer (RAFT)-mediated copolymerization of N-isopropylacrylamide with these macromonomers. It was found that the cloud point temperature of the graft copolymers almost linearly decreased from 32.1 to ∼14 °C, with increasing the content of the polyester macromonomer with a hydrophobic butyl end group in a copolymer chain from 0 to 17 wt %. A much smaller shift in the transition temperature (from 32.1 to ∼ 23 °C) was observed for the graft copolymers of N-isopropylacrylamide with polyesters bearing a polar hydroxyl group at the chain end. The thermoresponsive behavior dependence on the copolymer composition of the synthesized graft copolymers or their binary mixtures with poly(N-isopropylacrylamide) (PNIPAM) was also demonstrated in this study. Finally, it was proved that the obtained graft copolymers showed no cytotoxicity, and films prepared from these copolymers displayed better cell adhesion as compared to those prepared from neat PNIPAM.

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Section: Resultsmentioning

confidence: 99%

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Ksendzov

Nikishau

Зурина

et al. 2022

ACS Appl. Polym. Mater.

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“…This underestimation of M n by SEC calibrated against polystyrene standards for structurally similar carbazole-substituted styrenes was validated by performing SEC with a triple-detection system. This phenomenon is explained by the difference in the hydrodynamic volumes of the analyzed polymer and polystyrene with the same molecular weight . These data indicate that RAFT copolymerization of D1 with A1 , similarly to homopolymerization of D1 , proceeds in a controlled fashion, providing alternating copolymers with controlled molecular weight in a range between M n = 3000 and 12,000 g·mol –1 and moderate polydispersity ( Đ = 1.39–2.17).…”

Section: Resultsmentioning

confidence: 76%

“…Cyclic voltamperometry (CV) was used for the estimation of HOMO and LUMO energies of the synthesized monomers as well as of the alternating copolymers. A number of the previously reported works show that HOMO and LUMO energy levels of TSCT copolymers correspond to the levels of the monomers they were synthesized from. ,, All donor and acceptor monomers demonstrated quasi-reversible oxidation (Figure S17a–h), whereas voltammograms of alternating copolymers showed a much more complex behavior and were characterized by poor reproducibility (Figure S17i–x). Therefore, in line with our previous work, we used HOMO and LUMO energies of the monomers determined by CV (Table S2) to predict frontier orbital energies of the corresponding alternating copolymers.…”

Section: Resultsmentioning

confidence: 85%

“…47 The donor styrene-type monomers D3 and D4 were synthesized using the modified method applied earlier for the synthesis of carbazole-substituted styrene and perfluorostyrene. 51 10H-Phenoxazine (4.51 g, 24.6 mmol) (or 9,9-dimethylacridan (5.15 g, 24.6 mmol)), tris-(dibenzylideneacetone) dipalladium (0) (Pd 2 (dba) 3 , 0.6 g, 0.66 mmol), 1 M (t-Bu) 3 P in toluene (0.66 mL, 0.66 mmol), 4-bromostyrene (3 g, 16.38 mmol), and sodium tertbutoxide (9.42 g, 96.3 mmol) were dissolved under argon in 135 mL of dry toluene and stirred for 10 min at room temperature (preformation of the catalyst). The reaction mixture was heated at 90 °C for 4 h. After cooling, the reaction mixture was diluted with dichloromethane, and the organic phase was washed with water and brine.…”

Section: ■ Introductionmentioning

confidence: 99%

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Through-Space Charge-Transfer Thermally Activated Delayed Fluorescence Alternating Donor–Acceptor Copolymers for Nondoped Solution-Processable OLEDs

et al. 2023

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A series of donor−acceptor alternating copolymers with M n ≤ 12,000 g mol −1 and moderate polydispersity (Đ = 1.5− 2.5) were synthesized via RAFT copolymerization of styrene-based donor monomers and maleimide-type acceptor monomers in the presence of S-dodecyl-S′-(α,α′-dimethyl-α″-acetic acid)trithiocarbonate as a chain transfer agent. It was shown that synthesized alternating copolymers were characterized by high thermal stability (T d5 = 375−465 °C), and most of them exhibited exciplex emission via the through-space charge-transfer (TSCT) mechanism and displayed aggregation-induced emission. The color of the emission of synthesized copolymers largely depended on the nature of the acceptor monomer and could be changed from blue to orange depending on the copolymer structure. These copolymers in solid state demonstrated delayed fluorescence in the range between 0.35 and 6.2 μs and moderate photoluminescence quantum yield (2.12−6.32%) in air. Multicolor host-free solutionprocessable TADF OLEDs using synthesized alternating copolymers as emitters were fabricated, which showed good stability of electroluminescence spectra at different voltages. The highest external quantum efficiency of 7.84% was reached for the green emitting device.

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“…The experimental molecular weights are compared with theoretical molecular weights calculated based on the molar ratio of reagents and monomer conversion ( α ). We tried to determine the molecular masses of the synthesized polymers from 1 H NMR spectra analogically to the approach by Kostjuk and coworkers [ 28 ]. Unfortunately, in the 1 H spectra of the synthesized polymers, the signals of protons from the end groups (methyl and ethyl protons from the initiator moiety) overlap with protons’ signals from the main chain methyl and methylene protons (see Figure S1 in Supplementary Materials ).…”

Section: Resultsmentioning

confidence: 99%

New Photoresponsive Poly(meth)acrylates Bearing Azobenzene Moieties Obtained via ATRP Polymerization Exhibiting Liquid-Crystalline Behavior

2021

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Here, we report our studies on photoresponsive poly(meth)acrylates containing azobenzene groups connected to a polymer backbone via a short methylene linker. A series of side-chain azobenzene polymers was synthesized via the atom transfer radical polymerization (ATRP) technique using several catalytic systems. The polymers synthesized under the optimized conditions were characterized by a narrow polydispersity (Đ ≤ 1.35), and they underwent a reversible transformation of their structure under light illumination. The fabricated polymers can store and release energy accumulated during the UV-light illumination by the thermal cis-trans isomerization of the chromophore groups. The enthalpy of the process (determined from DSC) was relatively high and equaled 61.9 J∙g−1 (17 Wh∙kg−1), indicating a high potential of these materials in energy storage applications. The liquid-crystalline behavior of the synthesized poly(meth)acrylates was demonstrated by the birefringent optical textures as observed in thin-films and X-ray scattering studies.

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Atom-transfer radical homo- and copolymerization of carbazole-substituted styrene and perfluorostyrene

Cited by 5 publications

References 46 publications

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Through-Space Charge-Transfer Thermally Activated Delayed Fluorescence Alternating Donor–Acceptor Copolymers for Nondoped Solution-Processable OLEDs

New Photoresponsive Poly(meth)acrylates Bearing Azobenzene Moieties Obtained via ATRP Polymerization Exhibiting Liquid-Crystalline Behavior

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