Shuttling Motion in a Host-Guest Complex Triggered by Spiropyran to Merocyanine Reversible Chemical Transformation

J Org Chem. 2017 Apr 21;82(8):4484-4488. doi: 10.1021/acs.joc.7b00509. Epub 2017 Mar 30.

Abstract

A stimulus-responsive guest-containing spiropyran and viologen unit assembles with a 24-membered crown ether into a stable host-guest complex displaying a partially threaded geometry. Acid addition induces guest transformation to a merocyanine species activating a second recognition site, suitable for the formation of a pseudorotaxane. The simultaneous presence of two recognition sites produces a small-amplitude macrocycle shuttling motion, from the viologen to the merocyanine moiety. Base addition returns the guest to its spiropyran form, and concurrently the translation motion stops.

Publication types

  • Research Support, Non-U.S. Gov't