Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of <i>N</i>-Vinylnaphthalimide

Maki, Yuya; Mori, Hideharu; Endō, Takeshi

doi:10.1021/ma801359y

Cited by 22 publications

(25 citation statements)

References 65 publications

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“…St [72] VAc [389] VB [389] NVPI [220] VAc [391] VAc/VB [389] (NIPAM/369) [390] (Continued) [60] BA/AA [279] VAc [283] O S S 217* [381] 218 [392] O N 3 S S (NVCL) [384] (NVPI) [220] NVP [381] 366 [380] 367 [380] 368 [380] VAc [392] NVP-b-VAc [381] S O S O 219* OH 220 [169] …”

Section: Hnmentioning

confidence: 99%

“…B See footnote B of Table 3. GMA [398] St [398] tBMA/DEGMA [398] tBMA/DEGMA-b-GMA [398] MMA [88] 240 [283] S S N 241* S S N MA [399] NIPAM [400] 331 [401] NVPI [220] St [73] 332 [221] 336 [221] 338 [221] NIPAM/369 [390] (DMAM/369) [390] (MA/369) [390] St-b-331 [401] 242 S S N 243 [402,403] [229] MMA [402,403] 244 [404,405] 245 [406] S S N N N MA [406] MA [405] St [404] (Continued) 246* [406] S S N 247 [405] S S N BA [406] MA [406] OA [406] St [406] MA [405] N N S S 248 [405] N N S S C 9 H 19…”

Section: Hnmentioning

confidence: 99%

“…Styrene derivatives subjected to RAFT polymerization 348 [100,199] O 349 [138] O N N N 350 [158,309] N VBTAC 351 [159] Cl Ϫ Nϩ 352 [459] HN O 353 [321] O F F F F 354 [313] O F F F F 355 [313] [244] VBTPC 359 [34] Cl Ϫ P ϩ 360 [244] 361 [250] O N O 362 [207] O O O 363 [134] O O O Fe 364 [102] N 365 [102] N Table 23. Vinyl derivatives subjected to RAFT polymerization 366 [380] N 367 [380] N 368 [380] N 369 [390] N O O G. Moad, E. Rizzardo, and S. H. Thang [111,135] 370 [135,146] 375 [136] 376 [195] 377 [150] 378 [410] O O (H 3 C) 3 Si 372 [338,346,347] 373 [201] 374 [459] O [466] NAS 380 [160,299,317,345,347] 381 [178] 382 [222] [149,…”

Section: End-functional Polymers and End-group Transformationsmentioning

confidence: 99%

See 2 more Smart Citations

Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

905

720

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This paper provides a second update to the review of reversible deactivation radical polymerization achieved with thiocarbonylthio compounds (ZC(=S)SR) by a mechanism of reversible addition-fragmentation chain transfer (RAFT) that was published in June 2005 (Aust. J. Chem. 2005, 58, 379-410). The first update was published in November 2006 (Aust. J. Chem. 2006, 59, 669-692). This review cites over 500 papers that appeared during the period mid-2006 to mid-2009 covering various aspects of RAFT polymerization ranging from reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses and a diverse range of applications. Significant developments have occurred, particularly in the areas of novel RAFT agents, techniques for end-group removal and transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Hnmentioning

confidence: 99%

Section: Hnmentioning

confidence: 99%

Section: End-functional Polymers and End-group Transformationsmentioning

confidence: 99%

See 1 more Smart Citation

Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

905

720

View full text Add to dashboard Cite

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“…In contrast, dithiocarbamate-type CTAs in which the lone pair on the nitrogen atom is part of the aromatic pyrrole ring system, have been employed for the RAFT polymerization of conventional conjugated monomers such as styrene, 43,44 methyl acrylate 44 and N-isopropylacrylamide, 45 and have been used to polymerize less active monomers such as N-vinylphthalimide 46 and N-vinylnaphthalimide. 47 On the basis of the aforementioned results, we evaluated two R-designed tetrafunctional CTAs, including a CTA 1 and a CTA 2, as shown in Scheme 1. We initially studied the effectiveness of these tetrafunctional CTAs for the controlled radical polymerization of VEIBr and the synthesis of well-defined ionic liquid-type star polymers.…”

Section: Synthesis Of Poly(n-vinylimidazolium Salt) Starsmentioning

confidence: 99%

Temperature-responsive self-assembly of star block copolymers with poly(ionic liquid) segments

Mori

Ebina

Kambara

et al. 2012

Polym J

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Novel star block copolymers containing poly(N-vinylimidazolium salt) as a poly(ionic liquid) segment and poly(N-isopropylacrylamide) (poly(NIPAAm)) as a thermoresponsive segment were synthesized by reversible additionfragmentation chain transfer (RAFT) polymerization. Two R-designed tetrafunctional chain transfer agents (CTAs), including a xanthate-type CTA and a dithiocarbamate-type CTA, were compared for the polymerization of 1-ethyl-3-vinylimidazolium bromide (VEI-Br), which is an ionic liquid-type monomer. The dithiocarbamate-type tetrafunctional CTA was the most efficient CTA for the controlled synthesis of four-armed poly(VEI-Br) stars with low polydispersity values and controlled molecular weights. Star block copolymers with inner thermoresponsive segments connected to their core were synthesized by the RAFT polymerization of VEI-Br, using poly(NIPAAm) stars. In contrast, the RAFT polymerization of NIPAAm using poly(VEI-Br) stars afforded star block copolymers, with block arms consisting of outer block copolymer segments of thermoresponsive poly(NIPAAm). Thermally induced phase separation behavior and assembled structures of star block copolymers were studied in aqueous solution. Keywords: block copolymer; micelle; poly(ionic liquid); self-assembly; star polymer; star block copolymer; thermoresponsive polymer INTRODUCTION Recently, considerable attention has been paid to polymerized ionic liquids or polymeric ionic liquids, which are macromolecules obtained from the polymerization of ionic liquid monomers. [1][2][3] Polymeric ionic liquids with unique and attractive properties can be obtained by adjusting the structure of the cation (for example, imidazolium, pyridinium and tetraalkylammonium) and the anion (for example, halide, tetrafluoroborate and hexafluorophosphate). Potential applications of polymeric ionic liquids include polymeric electrolytes, catalytic membranes, ionic conductive materials, CO 2 absorbents, microwave absorbents and porous materials. Imidazolium salt is the most popular cation introduced into polymer backbones. A variety of polymers containing imidazolium moieties on their side chains have been developed, including poly(meth)acrylate, 4-7 polystyrene 8,9 and poly(N-vinyl imidazolium) 10-13 derivatives. The majority of these poly(ionic liquid)s were prepared by conventional radical polymerization. In addition to the structure of the substituent on the imidazolium ring, the solubility and properties of poly(Nvinylimidazolium salt) depend on the structure of the counteranion.As a result of recent progress in controlled radical polymerization (also known as controlled or living radical polymerization or reversible deactivation radical polymerization), well-defined block copolymers containing imidazolium moieties have been synthesized. 14,15 For example, Waymouth et al. 16,17 demonstrated the

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“…dithiocarbonates (xanthates) are useful for controlling the radical polymerization of O-vinyl and N-vinyl monomers such as vinyl acetate, [27][28][29] N-vinylpyrrolidone, [29,30] N-vinylcarbazole, [31][32][33] N-vinylindoles, [34] NVPI, [23] and N-vinylnaphthalimide. [35] In contrast, dithiocarbamatetype CTA 2, in which a nitrogen lone pair is part of an aromatic ring system, is used for the RAFT polymerization of conventional conjugated monomers such as styrene, [36,37] methyl acrylate, [37] and N-isopropylacrylamide (NIPAAm). [38] In the present study, the effects of the order of construction of the blocks and structure of the dithioesterend groups in the macro-CTAs were investigated in detail with regard to the controlled character of the polymerization and feasibility of manipulating the structures of the resulting block copolymers.…”

mentioning

confidence: 99%

Synthesis of Amphiphilic and Double‐Hydrophilic Block Copolymers Containing Poly(vinyl amine) Segments by RAFT Polymerization of N‐Vinylphthalimide

Maki¹,

Mori

Endō

2009

Macro Chemistry & Physics

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We report on the controlled synthesis of amphiphilic and double‐hydrophilic block copolymers having poly(vinyl amine) segments by the reversible addition–fragmentation chain transfer (RAFT) polymerization of N‐vinylphthalimide (NVPI), followed by deprotection. The block copolymer poly(NVPI)‐b‐poly(N‐isopropylacrylamide) with a controlled molecular weight and low molecular mass distribution was obtained by the polymerization of N‐isopropylacrylamide (NIPAAm) using dithiocarbamate‐terminated poly(NVPI). The chain extension from the dithiocarbamate‐terminated polystyrene to NVPI could be controlled well under suitable conditions, and provided the block copolymer, polystyrene‐b‐poly(NVPI). We also investigated the thermoresponsive and optoelectronic properties and the aggregation behavior of double hydrophilic and amphiphilic block copolymers obtained after deprotection.magnified image

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Synthesis of Well-Defined Alternating Copolymers by RAFT Copolymerization of N-Vinylnaphthalimide

Cited by 22 publications

References 65 publications

Living Radical Polymerization by the RAFT Process - A Second Update

Living Radical Polymerization by the RAFT Process - A Second Update

Temperature-responsive self-assembly of star block copolymers with poly(ionic liquid) segments

Synthesis of Amphiphilic and Double‐Hydrophilic Block Copolymers Containing Poly(vinyl amine) Segments by RAFT Polymerization of N‐Vinylphthalimide

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