Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 21, Pages 7054-7058Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201600628
Keywords
chirality; conformation analysis; resolution; solvent effects
Categories
Funding
- European Research Council [227897]
- Netherlands Organization for Scientific Research (NWO-CW)
- Ministry of Education, Culture and Science [024.001.035]
- NRSC
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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. H-1 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.
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