4.8 Article

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

Journal

ORGANIC LETTERS
Volume 21, Issue 15, Pages 5917-5921

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b02055

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Funding

  1. National Key Research and Development Program of China [2017YFA0402800]
  2. National Natural Science Foundation of China [51772285, 21473170]

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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 C-60 were investigated. This present work suggests an easily accessible Diels-Alder reaction strategy to synthesize cylindrical nanohoops.

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