Mechanochemical Synthesis of Corannulene: Scalable and Efficient Preparation of A Curved Polycyclic Aromatic Hydrocarbon under Ball Milling Conditions

Corannulene, a curved polycyclic aromatic hydrocarbon, is prepared in a multigram scale through mechanochemical synthesis. Initially, a mixer mill approach is examined and found to be suitable for a gram scale synthesis. For larger scales, planetary mills are used. For instance, 15 g of corannulene could be obtained in a single milling cycle with an isolated yield of 90 %. The yields are lower when the jar rotation rate is lower or higher than 400 revolutions per minute (rpm). Cumulatively, 98 g of corannulene is produced through the ball milling-based grinding techniques. These results indicate the future potential of mechanochemistry in the rational chemical synthesis of highly curved nanocarbons such as fullerenes and carbon nanotubes.

Automated summary

Corannulene, a curved polycyclic aromatic hydrocarbon, has been synthesized on a multigram scale using mechanochemical synthesis. While a mixer mill approach was suitable for gram-scale synthesis, larger scales utilized planetary mills. The yields were highest at a rotation rate of 400 rpm, with an isolated yield of 90% for 15g of corannulene obtained in a single milling cycle. In total, 98g of corannulene was produced using ball milling-based grinding techniques, highlighting the potential for mechanochemistry in the synthesis of highly curved nanocarbons.