jo8b02424_si_001.pdf (2.56 MB)
Synthesis and Photochemical Properties of Axially Chiral Bis(dinaphthofuran)
journal contribution
posted on 2018-10-30, 00:00 authored by Chiaki Katakami, Shogo Kamo, Ayame Torii, Nobuyuki Hara, Yoshitane Imai, Tohru Taniguchi, Kenji Monde, Yusuke Okabayashi, Takuya Hosokai, Kouji Kuramochi, Kazunori TsubakiBoth
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.