Creation of Hoop- and Bowl-Shaped Benzenoid Systems by Selective Detraction of [60]Fullerene Conjugation. [10]Cyclophenacene and Fused Corannulene Derivatives

Selective penta-addition of a methylcopper reagent followed by addition of a phenylcopper reagent
to a suitably modified synthetic intermediate results in creation of 40π-electron systemshoop- and bowl-shaped cyclic benzenoid compounds, [10]cyclophenacene, and dibenzo-fused corannulene derivatives.
The 40π-electron cyclophenacene derivatives have been found to be chemically stable, yellow-colored,
luminescent (560 nm), and EPR-silent. X-ray crystallographic analysis provided precision structural data
sets. The dibenzo-fused corannulene derivatives exhibit blue-green (460 nm) to red (649 nm) fluorescence.