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Rotaxanes with Dynamic Mechanical Chirality: Systematic Studies on Synthesis, Optical Resolution, Racemization, and Chiral-Prochiral Interconversion

preprint
submitted on 09.11.2019 and posted on 20.11.2019 by Fumitaka Ishiwari, Toshikazu Takata
Dynamic mechanical chirality of [2]rotaxane consisting of a Cs symmetric wheel and a C2v symmetric axle is discussed via the synthesis, optical resolution, racemization, and chiral-prochiral interconversion. This [2]rotaxane is achiral and/or prochiral when its wheel locates at the center of the axle, but becomes chiral when the wheel moves from the center of the axle. These were proved by the experiments on the optical resolution and racemization. The racemization energy of the optically resolved enantiomers was controlled by the bulkiness of the central substituents on the axle. Furthermore, the chiral-prochiral interconversion was achieved by relative positional control of the com-ponents. The present systematic studies will provide new insight into mechanically chiral interlocked compounds as well as the utility as dynamic chiral sources.

Funding

JSPS KAKENHI (15K13704)

ACT-C program (JST)

History

Email Address of Submitting Author

ishiwari@res.titech.ac.jp

Institution

Tokyo Institute of Technology

Country

Japan

ORCID For Submitting Author

0000-0002-0200-4510

Declaration of Conflict of Interest

The authors declare no competing financial interest.

Version Notes

Initial version

Exports