Selective synthesis and (chir)optical properties of binaphthyl-based chiral carbon macrocycles

Pengwei Fang; Muqing Chen; Xinyu Zhang; Pingwu Du

doi:10.1039/d2cc01242a

Selective synthesis and (chir)optical properties of binaphthyl-based chiral carbon macrocycles

Chem Commun (Camb). 2022 Jul 21;58(59):8278-8281. doi: 10.1039/d2cc01242a.

Authors

Pengwei Fang¹, Muqing Chen², Xinyu Zhang¹, Pingwu Du¹

Affiliations

¹ Hefei National Research Center for Physical Sciences at the Microscale, Anhui Laboratory of Advanced Photon Science and Technology, CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, iChEM, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui Province, 230026, China. dupingwu@ustc.edu.cn.
² School of Environment and Civil Engineering, Dongguan University of Technology, Dongguan, Guangdong Province, 523808, China. mqchen@ustc.edu.cn.

PMID: 35790128
DOI: 10.1039/d2cc01242a

Abstract

Herein, we report the selective synthesis, characterization, and photophysical properties of two novel chiral carbon macrocycles. Non-planar (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene was introduced into the scaffold of oligo-paraphenylenes to achieve the chirality in these macrocycles. Their photophysical properties were investigated by steady-state and time-resolved spectroscopies, as well as circular dichroism and circularly polarized luminescence spectroscopies. We demonstrate that the emission maxima of the chiral macrocycles are redshifted compared to chiral binaphthyl units and that macrocycles show chiroptical properties (|g_lum| > 1.0 × 10^-3).