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Chemistry. 2014 Jan 27;20(5):1272-8. doi: 10.1002/chem.201303486. Epub 2013 Dec 30.

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

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  • 1Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6-3 Aoba, Sendai 980-8578 (Japan), Fax: (+81) 22-795-6811.


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.

Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


equilibrium shift; helicenes; nanoparticles; precipitation; recognition

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