Synthesis and Photochemical
Properties of Axially
Chiral Bis(dinaphthofuran)
Version 2 2018-11-08, 19:27
Version 1 2018-11-08, 19:21
Posted on 2018-11-08 - 19:27
Both
enantiomers of axially chiral bis(dinaphthofuran) were prepared
in only two steps from 1′-hydroxy-4′-methoxy-2,2′-binaphthalenyl-1,4-dione,
followed by optical resolution via high-performance liquid chromatography
(HPLC) using a chiral stationary phase (CSP). The absolute configurations
were determined by comparison of experimental and calculated vibrational
circular dichroism (VCD) spectra. Synthetic bis(dinaphthofuran) exhibited
a broad and unstructured emission derived from an intramolecular excimer
in both solution and solid state. The methylene bridge brings both
chromophores close to each other and induces significant changes in
the photophysical behavior. Chiral bis(dinaphthofuran) displayed a
bathochromic shift in emission, as compared to the racemic mixture
in the solid state. Furthermore, the compounds showed high circularly
polarized luminescence (CPL) with a dissymmetry factor (glum) of 10–3 at 405 nm upon excitation
at 265 nm in a methanol solution. This compound serves as a model
for the design and synthesis of organic materials having CPL activity.
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Katakami, Chiaki; Kamo, Shogo; Torii, Ayame; Hara, Nobuyuki; Imai, Yoshitane; Taniguchi, Tohru; et al. (2018). Synthesis and Photochemical
Properties of Axially
Chiral Bis(dinaphthofuran). ACS Publications. Collection. https://doi.org/10.1021/acs.joc.8b02424
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AUTHORS (11)
CK
Chiaki Katakami
SK
Shogo Kamo
AT
Ayame Torii
NH
Nobuyuki Hara
YI
Yoshitane Imai
TT
Tohru Taniguchi
KM
Kenji Monde
YO
Yusuke Okabayashi
TH
Takuya Hosokai
KK
Kouji Kuramochi
KT
Kazunori Tsubaki