Journal of the American Chemical Society, Vol.140, No.16, 5334-5338, 2018
Binaphthyl-Bipyridyl Cyclic Dyads as a Chiroptical Switch
A series of chiral cyclic dyads, axially chiral binaphthyls linked to a 3,3'-bipyridyl, was synthesized. The dyad 2 bearing methoxy groups exhibited ON/OFF properties in circularly polarized luminescence (CPL), yielding a vertical bar g(lum)vertical bar of 1.6 X 10(-3) or 0 without any change in fluorescence. This type of CPL switch is unprecedented. Regioisomer 4 exhibited a dextro/levo rotation switching ability in [alpha](D). X-ray structures as well as experimental and theoretical analyses suggested that the switching properties depended on conformational changes.