Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

• DOI: 10.1021/jacs.9b06240
• Publication Date: 2019-07-19T15:34:03Z
• Authors: Kazuto Takaishi; Sakiko Hinoide; Tomoki Matsumoto; Tadashi Ema
• Keywords: 01 natural sciences; 0104 chemical sciences

A series of axially chiral peri-xanthenoxanthenes (PXXs) were synthesized from 1,1'-bi-2-naphthol without optical resolution. These are the first examples of chiral PXXs. Among them, PXX 5 with two naphthalene rings connected via a methylenedioxy bridge and a chiral axis displayed intense fluorescence (FL) and circularly polarized luminescence (CPL) both in solution (ΦFL of 0.72 and |glum| of 1.4 × 10-3) and in the solid state (ΦFL of 0.13 and |glum| of 4.8 × 10-3). The bridged structure of PXX 5 adjusts the angle between the vectors of the electric and magnetic transition dipole moments, which is essential for showing intense CPL activity.