Synthesis, structure, and aromaticity of a hoop-shaped cyclic benzenoid [10]cyclophenacene

The first hoop-shaped cyclic benzenoid compounds, [10]cyclophenacene derivatives that contain 40 π electrons, have been synthesized in three or four steps from [60]fullerene by rationally designed chemical modification. The compounds thus synthesized are chemically stable, yellow-colored, luminescent, and EPR-silent. X-ray crystallographic analysis provided high precision structural data sets. On the basis of these results and theoretical investigations, the new cyclic benzenoid molecules were proven to be aromatic. Copyright © 2003 American Chemical Society.