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

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.