Helicene-grafted silica nanoparticles capture hetero-double-helix intermediates during self-assembly gelation

Masamichi Miyagawa, Masahiko Yamaguchi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

A mixture of a pseudoenantiomeric ethynylhelicene (M)-tetramer and a (P)-pentamer forms a hetero-double-helix in a solution, which self-assembles and gelates solvents. When gelation was conducted in the presence of chiral silica (P)-nanoparticles grafted with (P)-helicene, the resulting hetero-double-helix intermediate was adsorbed on the (P)-nanoparticles, and was removed from the solution by aggregation and precipitation. The resulting precipitates contained only the hetero-double-helix, not random coil or clusters of the hetero-double-helix. (P)-Nanoparticles did not extract the hetero-double-helix from the self-assembly gels. The hetero-double-helix was then isolated by liberating it from the precipitates in 2-bromopropionic acid, and was crystallized from the solution. The crystalline hetero-double-helices were isolated for several other combinations of pseudoenantiomeric ethynylhelicene oligomers.

Original languageEnglish
Pages (from-to)8408-8415
Number of pages8
JournalChemistry - A European Journal
Volume21
Issue number23
DOIs
Publication statusPublished - 2015 Jun 1

Keywords

  • gels
  • nanoparticles
  • precipitation
  • reaction mechanisms
  • reactive intermediate
  • self-assembly

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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