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Published on: January 10, 2017
Dynamic Control of Chiral Recognition in Water-Soluble Naphthotubes Induced by Hydrostatic Pressure
Junnosuke Motoori1, Tomokazu Kinoshita1, Hongxin Chai2
1Department of Chemistry, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8551, Japan.
Abstract:
The dynamic control of chiral (enantiomeric) responses in chiral host-guest complexes through external stimuli is a significant challenge in modern chemistry for developing smart stimuli-responsive materials. Herein, we report the (chir)optical properties and chiral recognition behavior of water-soluble chiral naphthotubes (1) under the influence of hydrostatic pressure as an external stimulus. The hydrostatic pressure spectral profiles compared to those obtained at normal pressure revealed the dynamic behavior of 1 under hydrostatic pressure, owing to the flexible linker. In chiral recognition experiments, hydrophilic amino acids such as phenylalanine (Phe) and tryptophan (Trp) exhibited reaction volume changes (ΔV°) of -0.9 cm3 mol-1 for d-Phe, -1.2 cm3 mol-1 for l-Phe, -5.6 cm3 mol-1 for d-Trp, and -7.0 cm3 mol-1 for l-Trp, with enantioselectivity ranging from 1.2 to 1.6. In contrast, hydrophobic chiral styrene oxide (2) showed ΔV° values of 1.5 cm3 mol-1 for R-2 and 3.5 cm3 mol-1 for S- 2, with a relatively higher enantioselectivity of up to 7.6. These contrasting effects of hydrostatic pressure primarily originate from the dynamics of chiral naphthotubes.
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