Binaphthyl-Bipyridyl Cyclic Dyads as a Chiroptical Switch

J Am Chem Soc. 2018 Apr 25;140(16):5334-5338. doi: 10.1021/jacs.8b01860. Epub 2018 Apr 17.

Abstract

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 | glum| of 1.6 × 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 [α]D. X-ray structures as well as experimental and theoretical analyses suggested that the switching properties depended on conformational changes.

Publication types

  • Research Support, Non-U.S. Gov't