Enantiopure Functional Molecular Motors Obtained by a Switchable Chiral-Resolution Process
Journal
Chemistry ¡V A European Journal
Journal Volume
22
Journal Issue
21
Pages
7054-7058
Date Issued
2016
Author(s)
van Leeuwen, Thomas
Gan, Jefri
Kistemaker, Jos C. M.
Pizzolato, Stefano F.
Chang, Mu-Chieh
Feringa, Ben L.
Abstract
Molecular switches, rotors, and motors play an important role in the development of nano-machines and devices, as well as responsive and adaptive functional materials. For unidirectional rotors based on chiral overcrowded alkenes, their stereochemical homogeneity is of crucial importance. Herein, a method to obtain new and functionalizable overcrowded alkenes in enantiopure form is presented. The procedure involves a short synthesis of three steps and a solvent-switchable chiral resolution by using a readily available resolving agent. X-ray crystallography revealed the mode of binding of the motor with the resolving agent, as well as the absolute configuration of the motor. (1) H NMR and UV/Vis spectroscopy techniques were used to determine the dynamic behavior of this molecular motor. This method provides rapid access to ample amounts of enantiopure molecular motors, which will greatly facilitate the further development of responsive molecular systems based on chiral overcrowded alkenes.
Type
journal article