Synthesis and characterization of one-handed helical oligo(o-phenylene)s: control of axial chirality by planar chiral [2.2]paracyclophane

Asuka Yanagawa; Ryo Inoue; Yasuhiro Morisaki

doi:10.1039/d3cc05000a

Synthesis and characterization of one-handed helical oligo(o-phenylene)s: control of axial chirality by planar chiral [2.2]paracyclophane

Chem Commun (Camb). 2024 Feb 1;60(11):1468-1471. doi: 10.1039/d3cc05000a.

Authors

Asuka Yanagawa¹, Ryo Inoue¹, Yasuhiro Morisaki¹

Affiliation

¹ Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University, 1 Gakuen Uegahara, Sanda, Hyogo 669-1330, Japan. ryoinoue@kwansei.ac.jp.

PMID: 38223998
DOI: 10.1039/d3cc05000a

Abstract

Optically active oligo(o-phenylene)-layered molecules were synthesized from planar chiral enantiopure [2.2]paracyclophane. Their structures and optical properties were characterized by experimental and theoretical approaches. The axial chiralities between phenylene rings of the oligo(o-phenylene)s were controlled by the planar chirality to form one-handed helical structures. The o-quinquephenyl-layered molecule was emissive, and circularly polarized luminescence was observed with a high anisotropy factor (|g_lum| value) of 0.012.