Synthesis and Radical Polymerization of p-Phenylselenomethylstyrene and Applications to Graft Copolymers

Kwon, Tae Seok; Kondo, Shuji; Takagi, Koji; Kunisada, Hideo; Yuki, Yasuo

doi:10.1295/polymj.31.483

Cited by 26 publications

(33 citation statements)

References 20 publications

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“…21 The obtained polymer showed a controlled molecular weight. 21 The obtained polymer showed a controlled molecular weight.…”

Section: Polymerization Resultsmentioning

confidence: 94%

“…Such a transfer reaction may dominate in the initial stage due to the relatively high chain transfer constant of the diselenide, 25 which results in a significant induction period. The diselenide decomposes to the selenium centred radical 1 under the irradiation of light.…”

Section: Structure Analysismentioning

confidence: 99%

“…Kwon et al reported that photopolymerization in the presence of diphenyl diselenide (DPDS) afforded polystyrene carrying phenylseleno groups at both chain ends. 21,28,30,31 These polymers contained selenide chain ends, which could be oxidized to give the corresponding polymer with carbon-carbon double bonds. 22 After optimizing the selenide structure and polymerization conditions, polymers with different topologies were realized.…”

Section: Introductionmentioning

confidence: 99%

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Diselenide mediated controlled radical polymerization under visible light irradiation: mechanism investigation and α,ω-ditelechelic polymers

et al. 2015

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The radical polymerization of styrene was investigated in the presence of five diaryl diselenide compounds with different substitution groups on the benzene ring under visible light irradiation. It showed that bis-(2,6-dimethylphenyl) diselenide (DmXDS) with two methyl groups on every benzene ring was the most efficient mediator for preparing polymers with a predetermined molecular weight and narrow molecular weight distribution. The reasons were analyzed through a quantum calculation method. The polymerization behavior of styrene in the presence of DmXDS was further investigated in depth. The results showed a typical living radical polymerization process. Polymers retaining the selenide structures at both the αand ω-ends were verified by NMR and MALDI-TOF. Such end capped selenide groups could be transformed into terminal vinyl groups with a high efficiency under oxidative conditions, which offers a route to prepare "macromonomers" with a narrow molecular weight distribution. † Electronic supplementary information (ESI) available: The NMR spectra and UV-vis spectra of the diaryl diselenides, GPC curves of the polymers, and calculation results. See

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“…21 The obtained polymer showed a controlled molecular weight. 21 The obtained polymer showed a controlled molecular weight.…”

Section: Polymerization Resultsmentioning

confidence: 94%

Section: Structure Analysismentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Diselenide mediated controlled radical polymerization under visible light irradiation: mechanism investigation and α,ω-ditelechelic polymers

et al. 2015

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“…[1±7] Among them, the photoiniferter technique has been one of the techniques well known as a simple procedure, and a variety of monomers can be applied. [13] The resulting polystyrene (BPSE-PST) containing benzyl and phenylseleno groups at a-and o-chain ends, respectively, was obtained from this method. [8±11] We have already reported the very high radical capturing ability of diphenyl diselenide (DPDSE) in photopolymerization of styrene.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diblock Copolymers by End Functional Polystyrene Containing Phenylseleno Groups as Polymeric Photoiniferter

Kwon

Takagi

Kunisada

et al. 2002

Journal of Macromolecular Science, Part A

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Block copolymers of styrene and p-substituted styrene were prepared by photopolymerization of p-bromostyrene or p-methylstyrene in the presence of end functional polystyrene (DPDSE-PST) containing phenylseleno groups at the a and o-chain ends as polymeric photoiniferter. To determine the form of resulting block copolymers, the behavior of chain terminals of DPDSE-PST was investigated. The ability of photoinitiate and chain transfer of b-phenylethyl p-tert-butylphenyl selenide as a model compound of a-chain end of DPDSE-PST was much smaller than that of benzyl phenyl selenide as a model compound of o-chain end of DPDSE-PST. On the other hand, the polymerization of styrene, prepared by 1,4-Bis( p-tert-butylphenyl) diselenide as photoiniferter, with styrene also revealed a form of the resulting block copolymer was an AB block structure.

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“…Graft copolymers have generally been synthesized by macromonomer technology,1–4 by the linkage of two different polymers through polymer coupling reactions,5 or by the polymerization of a monomer from active sites on a backbone polymer 6, 7. Recently, much interest has been directed toward the precise control of such copolymerization parameters as the molecular weight, molecular weight distribution, and density of graft chains.…”

Section: Introductionmentioning

confidence: 99%

Preparation of a copolymer of methyl methacrylate and 2-(dimethylamino)ethyl methacrylate with pendant 4-benzyloxy-2,2,6,6-tetramethyl-1-piperidinyloxy and its initiation of the graft polymerization of styrene by a controlled radical mechanism

Sun¹,

Wan²,

Huang³

2001

J. Polym. Sci. A Polym. Chem.

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The macroinitiator of a copolymer (PMD BTM ) of methyl methacrylate (MMA) and 2-(dimethylamino)ethyl methacrylate (DAMA) with 4-benzyloxy-2,2,6,6tetramethyl-1-piperidinyloxy (BTEMPO) pendant groups was prepared by the photochemical reaction of tertiary amine groups of the copolymer with benzophenone in the presence of BTEMPO. The radical copolymerization of MMA and DAMA was carried out first with azo-bis-isobutyronitrile (AIBN) as an initiator; then, the dimethylamine groups of the copolymer constituted a charge-transfer complex with benzophenone under UV irradiation, and the methylene of ternary amine and diphenyl methanol radicals were produced. The former was capped by BTEMPO, and the nitroxide (BTEMPO) was attached to the polymeric backbone. The amount of pendant BTEMPO on PMD BTM was measured by 1 H NMR. PMD BTM initiated the graft polymerization of styrene via a controlled radical mechanism, and the molecular weight of the PMD-gpolystyrene increased with the polymerization time.

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Synthesis and Radical Polymerization of p-Phenylselenomethylstyrene and Applications to Graft Copolymers

Cited by 26 publications

References 20 publications

Diselenide mediated controlled radical polymerization under visible light irradiation: mechanism investigation and α,ω-ditelechelic polymers

Diselenide mediated controlled radical polymerization under visible light irradiation: mechanism investigation and α,ω-ditelechelic polymers

Synthesis of Diblock Copolymers by End Functional Polystyrene Containing Phenylseleno Groups as Polymeric Photoiniferter

Preparation of a copolymer of methyl methacrylate and 2-(dimethylamino)ethyl methacrylate with pendant 4-benzyloxy-2,2,6,6-tetramethyl-1-piperidinyloxy and its initiation of the graft polymerization of styrene by a controlled radical mechanism

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