Synthesis and Physical Properties of a Phenanthrene-Based [6,6] Hollow Bilayer Cylindrical Nanoring

Pingsen Huang; Guilin Zhuang; Shengda Wang; Xinyu Zhang; Pingwu Du

doi:10.1021/acs.orglett.1c02973

Synthesis and Physical Properties of a Phenanthrene-Based [6,6] Hollow Bilayer Cylindrical Nanoring

Org Lett. 2021 Oct 15;23(20):7976-7980. doi: 10.1021/acs.orglett.1c02973. Epub 2021 Oct 6.

Authors

Pingsen Huang¹, Guilin Zhuang², Shengda Wang¹, Xinyu Zhang¹, Pingwu Du¹

Affiliations

¹ Hefei National Laboratory for Physical Sciences at the Microscale, iChEM, CAS Key Laboratory of Materials for Energy Conversion, Department of Materials Science and Engineering, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui Province 230026, China.
² College of Chemical Engineering, Zhejiang University of Technology, 18 Chaowang Road, Hangzhou, Zhejiang Province 310032, China.

PMID: 34612035
DOI: 10.1021/acs.orglett.1c02973

Abstract

Herein, we report the synthesis and properties of a [6,6] hollow bilayer cylindrical nanoring (HBCNR) from a planar macrocycle via a Diels-Alder and Yamamoto coupling reaction. The fluorescence quantum yield of HBCNR was determined to be Φ_F = 52%, which is four times higher than its precursor. In addition, its hollow nanoring configuration was also simulated by theoretical studies, and the tension energy was estimated to be 47.1 kcal/mol.