Equilibrium shift in solution: Molecular shape recognition and precipitation of a synthetic double helix using helicene-grafted silica nanoparticles

Masamichi Miyagawa, Wataru Ichinose, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

Chiral silica nanoparticles (70 nm) grafted with (P)-helicene recognized the molecular shape of double helix and random coil (P)-ethynylhelicene oligomers in solution. A mixture of the (P)-nanoparticles and double helix precipitated much faster than a mixture of the (P)-nanoparticles and random coil, and the precipitate contained only the double helix. The mixture of the (P)-nanoparticles and (P)-ethynylhelicene pentamer reversibly dispersed in trifluoromethylbenzene upon heating at 708C and precipitated upon cooling at 258C. When a 10:90 equilibrium mixture of the double helix and random coil in solution was treated with the (P)-nanoparticles, the double helix was precipitated in 53% yield and was accompanied by equilibrium shift.

Original languageEnglish
Pages (from-to)1272-1278
Number of pages7
JournalChemistry - A European Journal
Volume20
Issue number5
DOIs
Publication statusPublished - 2014 Jan 27

Keywords

  • Equilibrium shift
  • Helicenes
  • Nanoparticles
  • Precipitation
  • Recognition

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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