180 degree unidirectional bond rotation in a biaryl lactone artificial molecular motor prototype.
A bifunctional biaryl lactone has been synthesized that should be capable of iterative unidirectional aryl-aryl bond rotation via: (1) a diastereoselective lactone ring opening, (S)-1 to (P,S)-2 or (M,S)-2; (2) a chemoselective lactonization, (P,S)-2 or (M,S)-2 to (S)-3; and (3) a chemoselective hydrolysis, (S)-3 to (S)-1. Preliminary results of a racemic sample have indicated unidirectional 180 degrees rotation with very high directional selectivity per individual artificial molecular motor molecule through the first two steps of this sequence. [reaction: see text]
Dahl
Bart J
BJ
Department of Chemistry and Materials Science Institute, University of Oregon, Eugene, OR 97403, USA.
Branchaud
Bruce P
BP
D001894:Borohydrides / Q000737:chemistry; D006868:Hydrolysis; D007700:Kinetics; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D012995:Solubility; D013237:Stereoisomerism
D001894:Borohydrides; D007783:Lactones; C025364:sodium borohydride