van Leeuwen Thomas, Gan Jefri, Kistemaker Jos C M, Pizzolato Stefano F, Chang Mu-Chieh, Feringa Ben L
Centre for Systems Chemistry, Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG, Groningen, The Netherlands.
Chemistry. 2016 May 17;22(21):7054-8. doi: 10.1002/chem.201600628. Epub 2016 Apr 13.
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.
分子开关、转子和马达在纳米机器与器件以及响应性和适应性功能材料的发展中发挥着重要作用。对于基于手性过度拥挤烯烃的单向转子而言，其立体化学均一性至关重要。在此，介绍一种以对映体纯形式获得新型且可功能化的过度拥挤烯烃的方法。该过程包括三步短合成以及通过使用一种易得的拆分剂进行溶剂可切换的手性拆分。X射线晶体学揭示了马达与拆分剂的结合模式以及马达的绝对构型。使用（1）H NMR和紫外/可见光谱技术来确定该分子马达的动态行为。此方法能够快速获取大量对映体纯的分子马达，这将极大地促进基于手性过度拥挤烯烃的响应性分子体系的进一步发展。
