Holding of planar chirality of pillar[5]arene by kinetic trapping using host–guest interactions with achiral guest solvents
Yuuya Nagata, Misaki Suzuki, Y. Shimada, Hiroki Sengoku, Shungo Nishida, Takahiro Kakuta, Tada‐aki Yamagishi, Michinori Suginome, Tomoki Ogoshi
Abstract
We report a solvent-dependent switching and holding of planar chirality of pillar[5]arene with stereogenic carbons at both rims by host-guest complexation with achiral guest solvents. The planar chirality could be held for a given length of time at 25 °C in long linear guest solvents by kinetic trapping through host-guest complexation. The kinetic trapping worked at 25 °C, but not at 60 °C, thus a planar-chiral inversion using kinetic trapping based on host-guest complexation in the long linear solvents was demonstrated.
Topics & Concepts
Chirality (physics)StereocenterTrappingKinetic energyPlanarChemistrySolventPlanar chiralityPillarChemical physicsCrystallographySolvent polarityOrganic chemistryEnantioselective synthesisCatalysisQuantum mechanicsStructural engineeringComputer graphics (images)BiologyPhysicsNambu–Jona-Lasinio modelEngineeringComputer scienceEcologyQuarkChiral symmetry breakingSupramolecular Chemistry and ComplexesAdvanced NMR Techniques and ApplicationsMolecular spectroscopy and chirality