Issue 3, 2023

Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane: a chiral building block for optically active helicene-stacked molecules emitting circularly polarized luminescence

Abstract

Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane was achieved using the diastereomer method. Optically active π-stacked molecules consisting of phenanthrene and benzo[c]phenanthrene were synthesized using the enantiopure pseudo-para-disubstituted [2.2]paracyclophanes as chiral building blocks. Helicity was induced on the stacked phenanthrene and benzo[c]phenanthrene moieties by the planar chiral [2.2]paracyclophane, and the molecule formed an optically active S-shaped structure. The S-shaped molecule emitted circularly polarized luminescence, which was compared with that of the corresponding optically active U-shaped molecule prepared from pseudo-meta-disubstituted [2.2]paracyclophane.

Graphical abstract: Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane: a chiral building block for optically active helicene-stacked molecules emitting circularly polarized luminescence

Supplementary files

Article information

Article type
Paper
Submitted
02 Nov. 2022
Accepted
18 Dec. 2022
First published
20 Dec. 2022

J. Mater. Chem. C, 2023,11, 986-993

Optical resolution of pseudo-para-disubstituted [2.2]paracyclophane: a chiral building block for optically active helicene-stacked molecules emitting circularly polarized luminescence

A. Yanagawa, M. Tsuchiya, R. Inoue and Y. Morisaki, J. Mater. Chem. C, 2023, 11, 986 DOI: 10.1039/D2TC04652K

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