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Published on: September 13, 2024
Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence
Yuki Nojima1, Masashi Hasegawa, Nobuyuki Hara
1Department of Chemistry, Graduate School of Science, Kitasato University, 1-15-1 Kitasato, Minami-ku, Sagamihara, Kanagawa 252-0373, Japan. masasi.h@kitasato-u.ac.jp.
Abstract:
A series of cyclic oligomers with Dn symmetry (n = 2-5) based on chiral (R)/(S)-binaphthyl exhibiting intensive chiroptical properties were synthesized by using a Ni(0)-catalyzed coupling reaction. The intensity and the handedness of circularly polarized luminescence (CPL) were dependent on the ring size of the cyclic oligomers, in which the 1,1'-binaphthyl moieties form s-cis (n = 2, 3) or s-trans (n = 4, 5) conformers in the excited state. The relationship between the structure and chiroptical properties is discussed with the aid of X-ray analysis and DFT calculations.
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