Inductive effect-assisted chain-growth polycondensation. Synthetic development from para- to meta-substituted aromatic polyamides with low polydispersities

Ryuji Sugi, Akihiro Yokoyama, Taniyuki Furuyama, Masanobu Uchiyama, Tsutomu Yokozawa

Research output: Contribution to journalArticlepeer-review

60 Citations (Scopus)

Abstract

The polycondensation of m-(octylamino)benzoic acid esters (1) with base was investigated in order to extend the synthesis of well-defined condensation polymers from para-substituted polymers to meta-substituted ones. We expected that the aminyl anion of 2 would deactivate the ester moiety at the meta position of 2 owing to the strong inductive effect of the anion, resulting in, not self-polycondensation, but chain-growth polycondensation. The methyl ester monomer 1a polymerized with lithium hexamethyldisilazide (LiHMDS) in the presence of phenyl benzoate (3a) as an initiator at 0 °C to afford a polymer with a low polydispersity, but the product contained a small amount of self-condensation polymer. On the other hand, the polymerization of the ethyl ester monomer (1b) with phenyl 4-methylbenzoate (3b) proceeded through chain polymerization without self-polycondensation. The M n values of the polymers increased linearly in proportion to the [1b] 0/[3b] 0 ratio, and the M w/M n ratios remained narrow over the entire [1b] 0/[3b] 0 range. Furthermore, a block copolymer of N-alkylated poly(m-benzamide) and poly(p-benzamide) with a low polydispersity was synthesized by the monomer addition method under this polymerization condition.

Original languageEnglish
Pages (from-to)10172-10173
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number29
DOIs
Publication statusPublished - 2005 Jul 27

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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