Synthesis of Sequence-Specific Polymers with Amide Side Chains via Regio-/Stereoselective Ring-Opening Metathesis Polymerization of 3-Substituted cis-Cyclooctene

Kohei Osawa, Shingo Kobayashi, Masaru Tanaka

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Highly regio-/stereoregular (trans-head-to-tail) polymers with amide side chains on every eighth backbone carbon were successfully synthesized by ring-opening metathesis polymerization (ROMP) of 3-substituted cis-cyclooctene (3RCOE) using Grubbs second-generation catalyst (G2). Regioregular linear ethylene-acrylamide copolymers were also prepared via hydrogenation of the obtained poly(3RCOE)s. The thermal properties and solubility of the obtained polymers were strongly influenced by the presence of amide hydrogen in the side chains, the presence of unsaturated bonds in the carbon backbone, and the side chain density. The presence of amide hydrogen in the side chains resulted in the formation of crystalline polymers and the lack of solubility of these polymers in common organic solvents. In contrast, the absence of amide hydrogen in the side chains led to the formation of amorphous polymers exhibiting good solubility in common organic solvents, and decreasing values of T g were observed for amorphous polymers as a result of the saturation of double bonds in the backbone via hydrogenation.

Original languageEnglish
Pages (from-to)8154-8161
Number of pages8
JournalMacromolecules
Volume49
Issue number21
DOIs
Publication statusPublished - Nov 8 2016

Fingerprint

Ring opening polymerization
Amides
Polymers
Hydrogen
Solubility
Organic solvents
Hydrogenation
Carbon
Acrylamide
Ethylene
Thermodynamic properties
Copolymers
Crystalline materials
Catalysts

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics
  • Inorganic Chemistry
  • Materials Chemistry

Cite this

Synthesis of Sequence-Specific Polymers with Amide Side Chains via Regio-/Stereoselective Ring-Opening Metathesis Polymerization of 3-Substituted cis-Cyclooctene. / Osawa, Kohei; Kobayashi, Shingo; Tanaka, Masaru.

In: Macromolecules, Vol. 49, No. 21, 08.11.2016, p. 8154-8161.

Research output: Contribution to journalArticle

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abstract = "Highly regio-/stereoregular (trans-head-to-tail) polymers with amide side chains on every eighth backbone carbon were successfully synthesized by ring-opening metathesis polymerization (ROMP) of 3-substituted cis-cyclooctene (3RCOE) using Grubbs second-generation catalyst (G2). Regioregular linear ethylene-acrylamide copolymers were also prepared via hydrogenation of the obtained poly(3RCOE)s. The thermal properties and solubility of the obtained polymers were strongly influenced by the presence of amide hydrogen in the side chains, the presence of unsaturated bonds in the carbon backbone, and the side chain density. The presence of amide hydrogen in the side chains resulted in the formation of crystalline polymers and the lack of solubility of these polymers in common organic solvents. In contrast, the absence of amide hydrogen in the side chains led to the formation of amorphous polymers exhibiting good solubility in common organic solvents, and decreasing values of T g were observed for amorphous polymers as a result of the saturation of double bonds in the backbone via hydrogenation.",
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