Premium
Enantiopure Functional Molecular Motors Obtained by a Switchable Chiral‐Resolution Process
Author(s) -
van Leeuwen Thomas,
Gan Jefri,
Kistemaker Jos C. M.,
Pizzolato Stefano F.,
Chang MuChieh,
Feringa Ben L.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600628
Subject(s) - enantiopure drug , resolution (logic) , process (computing) , molecular motor , computer science , chemistry , materials science , nanotechnology , artificial intelligence , organic chemistry , enantioselective synthesis , programming language , catalysis
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.