180° 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° rotation with very high
directional selectivity per individual artificial molecular motor molecule through the first two steps of this sequence.

已合成一种双功能联芳基内酯（bifunctional biaryl lactone），该化合物可通过以下路径实现迭代式单向芳基-芳基键旋转：(1) 非对映选择性内酯开环：将(S)-1转化为(P,S)-2或(M,S)-2；(2) 化学选择性内酯化：将(P,S)-2或(M,S)-2转化为(S)-3；(3) 化学选择性水解：将(S)-3转化为(S)-1。对外消旋样品的初步研究结果显示，通过该序列的前两步，每个人工分子马达（artificial molecular motor）分子均可实现具有极高方向选择性的180°单向旋转。