Aminomethylenehelicene oligomers possessing flexible two-atom linker form a stimuli-responsive double-helix in solution

Masanori Shigeno, Masahiko Sato, Yo Kushida, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

14 Citations (Scopus)

Abstract

Aminomethylenehelicene oligomers up to the (M)-heptamer were synthesized by reductive amination from a formylhelicene building block. The oligomers containing more than three helicenes formed a double helix in 1,3-dilfuorobenzene. The (M)-tetramer and (M)-pentamer unfolded into a random coil by heating to 60°C, whereas the (M)-hexamer only slightly unfolded at the same temperature. A two-sided thermal hysteresis was detected in the structural change of the (M)-tetramer and (M)-pentamer during cooling and heating. The (M)-pentamer and (M)-hexamer unfolded with the addition of trifluoroacetic acid and regenerated a double helix with the addition of triethylamine.

Original languageEnglish
Pages (from-to)797-804
Number of pages8
JournalAsian Journal of Organic Chemistry
Volume3
Issue number7
DOIs
Publication statusPublished - 2014 Jul

Keywords

  • Acid/base responses
  • Aminomethylenehelicenes
  • Helical structures
  • Oligomers
  • Thermal hysteresis

ASJC Scopus subject areas

  • Organic Chemistry

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