Reaction Control in Condensation Polymerization

Yokozawa, Tsutomu; Ajioka, Naomi; Yokoyama, Akihiro

doi:10.1007/12_2007_125

Cited by 7 publications

(7 citation statements)

References 319 publications

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“…Local conformational preferences of the growing oligomeric chain correlate with the substitution pattern of the electrophilic monomer, and a model has been described that allows facile prediction of reaction outcomes for a given electrophilic substrate. As reported for many other AA−BB polycondensation processes, , we found that in certain cases (i.e., syn -biased systems) the observed product ratios do not follow classical theory for the relationship between concentration and the resulting macrocycle to polymer ratio. Depending on the substitution pattern on the electrophilic monomer, macrocycle formation is kinetically driven to favor macrocycles regardless of concentration.…”

Section: Discussionsupporting

confidence: 50%

Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes

Wackerly¹,

Meyer²,

Crannell³

et al. 2009

Macromolecules

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We report a high yielding AA−BB type step-growth synthesis of poly(m-phenylene oxides) (mPOs) by nucleophilic aromatic substitution (SNAr) reactions. Previously, poly(mPOs) have proven difficult to synthesize, especially by SNAr, due to competing cyclooligomer (oxacalixarene) formation. We have found that the linear (polymeric) vs cyclic (oligomeric) product distribution is strongly dependent on the substitution pattern of the electrophilic monomer, and a model is described that predicts whether the reacting monomers will kinetically favor formation of poly(mPOs) or oxacalixarenes. The polycondensation reaction tolerates a range of functional groups on both reactive monomers, and the synthesized poly(mPOs) have high thermal and aqueous stability but are readily depolymerized in polar aprotic media.

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Section: Discussionsupporting

confidence: 50%

Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes

Wackerly¹,

Meyer²,

Crannell³

et al. 2009

Macromolecules

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“…This diblock copolymer self-assembled in THF to form spherical aggregates. Block copolymer of the aromatic polyether and poly(methyl methacrylate) was prepared by a similar approach . However, block copolymer of the aromatic polyether and polyacrylonitrile was synthesized in a reverse order of polymerization, because polyacrylonitrile macroinitiator underwent degradation with 21a under the conditions for the polymerization of 21a …”

Section: P-substituted Aromatic Condensation Polymers: Polymerization...mentioning

confidence: 99%

Chain-Growth Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and π-Conjugated Polymers

2009

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“…Recently, rod‐coil block copolymers consisting of condensation and addition blocks have been studied, but most of them do not have a precisely defined condensation block mainly because of synthetic difficulties 3. However, a recent development of chain‐growth condensation polymerization (CGCP) has opened an easy access for rod‐coil block copolymers containing condensation and addition blocks 4…”

Section: Introductionmentioning

confidence: 99%

Synthesis of well‐defined rod‐coil block copolymers containing trifluoromethylated poly(phenylene oxide)s by chain‐growth condensation polymerization and atom transfer radical polymerization

Kim

Seo

Kim

2010

J. Polym. Sci. A Polym. Chem.

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Well-defined trifluoromethylated poly(phenylene oxide)s were synthesized via nucleophilic aromatic substitution (S N Ar) reaction by a chain-growth polymerization manner. Polymerization of potassium 4-fluoro-3-(trifluoromethyl)phenolate in the presence of an appropriate initiator yielded polymers with molecular weights of $4000 and polydispersity indices of <1.2, which were characterized by 1 H nuclear magnetic resonance spectroscopy and gel permeation chromatography. Initiating sites for atom transfer radical polymerization (ATRP) were introduced at the either side of chain ends of the poly(phenylene ox-ide), and used for ATRP of styrene and methyl methacrylate, yielding well-defined rod-coil block copolymers. Differential scanning calorimetry study indicated that the well-defined trifluoromethylated poly(phenylene oxide)s showed high crystallinity and were immiscible with polystyrene. EXPERIMENTALMaterials 4-Fluoro-3-(trifluoromethyl)phenol (Fluorochem), 4-fluoro-3-(trifluoromethyl)aniline (Aldrich), 4-nitro-3-(trifluoromethyl)benzonitrile (2, Aldrich), 2-bromoisobutyryl bromide (Aldrich), and 2,2 0 -bipyridine (bpy, Aldrich) were used as received. Phenol was distilled under reduced pressure. 2-*Present address:

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Reaction Control in Condensation Polymerization

Cited by 7 publications

References 319 publications

Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes

Selective Synthesis of Poly(m-phenylene oxides) over Oxacalixarenes

Chain-Growth Condensation Polymerization for the Synthesis of Well-Defined Condensation Polymers and π-Conjugated Polymers

Synthesis of well‐defined rod‐coil block copolymers containing trifluoromethylated poly(phenylene oxide)s by chain‐growth condensation polymerization and atom transfer radical polymerization

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