From Planar Macrocycle to Cylindrical Molecule: Synthesis and Properties of a Phenanthrene-Based Coronal Nanohoop as a Segment of [6,6]Carbon Nanotube

Shengsheng Cui; Qiang Huang; Jinyi Wang; Hongxing Jia; Pingsen Huang; Shengda Wang; Pingwu Du

doi:10.1021/acs.orglett.9b02055

From Planar Macrocycle to Cylindrical Molecule: Synthesis and Properties of a Phenanthrene-Based Coronal Nanohoop as a Segment of [6,6]Carbon Nanotube

Org Lett. 2019 Aug 2;21(15):5917-5921. doi: 10.1021/acs.orglett.9b02055. Epub 2019 Jul 22.

Authors

Shengsheng Cui¹, Qiang Huang¹, Jinyi Wang¹, Hongxing Jia¹, Pingsen Huang¹, Shengda Wang¹, Pingwu Du¹

Affiliation

¹ Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Materials for Energy Conversion, iChEM, Department of Materials Science and Engineering , University of Science and Technology of China (USTC) , 96 Jinzhai Road , Hefei , Anhui Province 230026 , China.

PMID: 31329458
DOI: 10.1021/acs.orglett.9b02055

Abstract

Herein, we explore phenanthrene as the building block to synthesize a hoop-shaped [6,6]carbon nanotube segment from a planar macocycle via a Diels-Alder reaction. The phenanthrene-based coronal nanohoop 7 was fully characterized by HR-MS, NMR, and other spectroscopies. In addition, its photophysical properties and the supramolecular interactions between 7 and fullerene C₆₀ were investigated. This present work suggests an easily accessible Diels-Alder reaction strategy to synthesize cylindrical nanohoops.