Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

Kazuto Takaishi; Sakiko Hinoide; Tomoki Matsumoto; Tadashi Ema

doi:10.1021/jacs.9b06240

Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

J Am Chem Soc. 2019 Jul 31;141(30):11852-11857. doi: 10.1021/jacs.9b06240. Epub 2019 Jul 22.

Authors

Kazuto Takaishi¹, Sakiko Hinoide¹, Tomoki Matsumoto¹, Tadashi Ema¹

Affiliation

¹ Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , Tsushima , Okayama 700-8530 , Japan.

PMID: 31322357
DOI: 10.1021/jacs.9b06240

Abstract

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 (Φ_FL of 0.72 and |g_lum| of 1.4 × 10^-3) and in the solid state (Φ_FL of 0.13 and |g_lum| 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.

Publication types

Research Support, Non-U.S. Gov't