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

Kazuto Takaishi, Sakiko Hinoide, Tomoki Matsumoto, Tadashi Ema

Research output: Contribution to journal › Article

8 Citations (Scopus)

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.

Original language	English
Pages (from-to)	11852-11857
Number of pages	6
Journal	Journal of the American Chemical Society
Volume	141
Issue number	30
DOIs	https://doi.org/10.1021/jacs.9b06240
Publication status	Published - Jul 31 2019

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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Takaishi, K., Hinoide, S., Matsumoto, T., & Ema, T. (2019). Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore. Journal of the American Chemical Society, 141(30), 11852-11857. https://doi.org/10.1021/jacs.9b06240

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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 (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.",

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