Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

Kazuto Takaishi, Sakiko Hinoide, Tomoki Matsumoto, Tadashi Ema

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)11852-11857
Number of pages6
JournalJournal of the American Chemical Society
Volume141
Issue number30
DOIs
Publication statusPublished - Jul 31 2019

Fingerprint

Fluorescence
Luminescence
Naphthol
Dipole moment
Naphthalene
2-naphthol
naphthalene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore. / Takaishi, Kazuto; Hinoide, Sakiko; Matsumoto, Tomoki; Ema, Tadashi.

In: Journal of the American Chemical Society, Vol. 141, No. 30, 31.07.2019, p. 11852-11857.

Research output: Contribution to journalArticle

@article{7eab205bcb454260992b57d6c934a0ed,
title = "Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore",
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.",
author = "Kazuto Takaishi and Sakiko Hinoide and Tomoki Matsumoto and Tadashi Ema",
year = "2019",
month = "7",
day = "31",
doi = "10.1021/jacs.9b06240",
language = "English",
volume = "141",
pages = "11852--11857",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "30",

}

TY - JOUR

T1 - Axially Chiral peri-Xanthenoxanthenes as a Circularly Polarized Luminophore

AU - Takaishi, Kazuto

AU - Hinoide, Sakiko

AU - Matsumoto, Tomoki

AU - Ema, Tadashi

PY - 2019/7/31

Y1 - 2019/7/31

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85070532372&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85070532372&partnerID=8YFLogxK

U2 - 10.1021/jacs.9b06240

DO - 10.1021/jacs.9b06240

M3 - Article

C2 - 31322357

AN - SCOPUS:85070532372

VL - 141

SP - 11852

EP - 11857

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 30

ER -