Folding of dihelicenetriamines in water

Shinobu Honzawa, Hitoshi Okubo, Keiichi Nakamura, Shuzo Anzai, Masahiko Yamaguchi, Chizuko Kabuto

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Diastereomeric triamines containing two helicene moieties, 1,12-dimethylbenzo[c]phenanthrene, were synthesized and found to form folded structures in the water. Such folding was not observed for an achiral compound possessing a naphthalene moiety. The (M,M)-dihelicenetriamine with matching configuration at the helicene moieties formed a more stable folded structure than the (P,M)-isomer containing two enantiomeric helicene groups. The most stable folded conformation was predicted by the Monte Carlo method with Amber force field of the dihelicenetriamine.

Original languageEnglish
Pages (from-to)1043-1052
Number of pages10
JournalTetrahedron Asymmetry
Volume13
Issue number10
DOIs
Publication statusPublished - 2002 Jun 10

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Honzawa, S., Okubo, H., Nakamura, K., Anzai, S., Yamaguchi, M., & Kabuto, C. (2002). Folding of dihelicenetriamines in water. Tetrahedron Asymmetry, 13(10), 1043-1052. https://doi.org/10.1016/S0957-4166(02)00249-5