ol062428u_si_001.pdf (3.28 MB)

180° Unidirectional Bond Rotation in a Biaryl Lactone Artificial Molecular Motor Prototype

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journal contribution
posted on 07.12.2006 by Bart J. Dahl, Bruce P. Branchaud
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° rotation with very high directional selectivity per individual artificial molecular motor molecule through the first two steps of this sequence.