Binaphthyl–Bipyridyl Cyclic Dyads as a Chiroptical Switch

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 |g lum| of 1.6 × 10–3 or 0 without any change in fluorescence. This type of CP...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 140; no. 16; pp. 5334 - 5338
Main Authors Takaishi, Kazuto, Yasui, Makoto, Ema, Tadashi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 25.04.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
CIRCULARLY-POLARIZED LUMINESCENCE
HELIX
POLYACETYLENE
INVERSION
FOLDAMERS
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Summary: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 |g lum| 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.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b01860