Issue 19, 2019

Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence (CPL)

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.

Graphical abstract: Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence (CPL)

Supplementary files

Article information

Article type
Communication
Submitted
09 Nov 2018
Accepted
03 Jan 2019
First published
04 Jan 2019

Chem. Commun., 2019,55, 2749-2752

Stereogenic cyclic oligonaphthalenes displaying ring size-dependent handedness of circularly polarized luminescence (CPL)

Y. Nojima, M. Hasegawa, N. Hara, Y. Imai and Y. Mazaki, Chem. Commun., 2019, 55, 2749 DOI: 10.1039/C8CC08929A

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