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Equilibrium Shift in Solution: Molecular Shape Recognition and Precipitation of a Synthetic Double Helix Using Helicene‐Grafted Silica Nanoparticles
Author(s) -
Miyagawa Masamichi,
Ichinose Wataru,
Yamaguchi Masahiko
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201303486
Subject(s) - random coil , helix (gastropod) , nanoparticle , pentamer , helicene , triple helix , materials science , yield (engineering) , chemical engineering , crystallography , chemistry , nanotechnology , molecule , stereochemistry , organic chemistry , circular dichroism , composite material , engineering , ecology , biochemistry , snail , biology
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 70 °C and precipitated upon cooling at 25 °C. 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.