Synthesis and Photophysical Properties of a Chiral Carbon Nanoring Containing Rubicene

Xin Kong; Xinyu Zhang; Bing Yuan; Wen Zhang; Dapeng Lu; Pingwu Du

doi:10.1021/acs.joc.4c00387

Synthesis and Photophysical Properties of a Chiral Carbon Nanoring Containing Rubicene

J Org Chem. 2024 Jun 7;89(11):8255-8261. doi: 10.1021/acs.joc.4c00387. Epub 2024 May 21.

Authors

Xin Kong¹, Xinyu Zhang¹, Bing Yuan¹, Wen Zhang¹, Dapeng Lu², Pingwu Du¹

Affiliations

¹ Hefei National Research Center for Physical Sciences at 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, P. R. China.
² Inflammation and Immune Mediated Diseases Laboratory of Anhui Province, Anhui Institute of Innovative Drugs, School of Pharmacy, Anhui Medical University, 81 Meishan Road, Hefei, Anhui Province 230032, P. R. China.

PMID: 38771292
DOI: 10.1021/acs.joc.4c00387

Abstract

Herein we report the construction of an inherently chiral carbon nanoring, cyclo[7]paraphenylene-2,9-rubicene ([7]CPPRu_2,9), by combining rubicene with a C-shaped synthon through the Suzuki-Miyaura coupling reaction. The structure was fully confirmed by high-resolution mass spectroscopies (HR-MS) and various NMR techniques. The photophysical properties were investigated by UV-vis absorption and fluorescence spectroscopy as well as the time-resolved fluorescence decay. Moreover, two enantiomers (M)/(P)-[7]CPPRu_2,9 were successfully resolved by recyclable HPLC and studied by CD and CPL spectra.