Helical structures of N-alkylated poly(p-benzarnide)s

Aya Tanatani, Akihiro Yokoyama, Isao Azumaya, Yoshinori Takakura, Chikashi Mitsui, Motoo Shiro, Masanobu Uchiyama, Atsuya Muranaka, Nagao Kobayashi, Tsutomu Yokozawa

Research output: Contribution to journalArticlepeer-review

134 Citations (Scopus)

Abstract

Poly(p-benzamide)s 1 bearing a chiral side chain on the nitrogen atom were synthesized by chain-growth polycondensation methodology. The polyamides exhibited well-defined molecular weights with narrow polydispersities. Solutions of the polyamides in several organic solvents (CH3CN, CHCl 3, and CH3OH) showed dispersion type CD signals characteristic of coupled-oscillator and much larger as compared with the corresponding monomer. The CD signals were dependent on the temperature and molecular weight of the polyamides but independent of the solvent, as far as examined. An exciton model analysis of the absorption and CD spectra provided a clear-cut picture for the secondary structure of these polyamides in solution that the N-alkylated poly(p-benzamide)s possess a right-handed helical conformation ((P)-helix). In the solid states, the results of X-ray crystallographic analysis of 4-(methylamino)benzoic acid oligomers substantiated that they have a helical conformation with three monomer units per turn.

Original languageEnglish
Pages (from-to)8553-8561
Number of pages9
JournalJournal of the American Chemical Society
Volume127
Issue number23
DOIs
Publication statusPublished - 2005 Jun 15

ASJC Scopus subject areas

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

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