Abstract
The transformation of planar aromatic molecules into π-extended non-planar structures is a challenging task and has not been realized by mechanochemistry before. Here we report that mechanochemical forces can successfully transform a planar polyarene into a curved geometry by creating new C-C bonds along the rim of the molecular structure. In doing so, mechanochemistry does not require inert conditions or organic solvents and provide better yields within shorter reaction times. This is illustrated in a 20-minute synthesis of corannulene, a fragment of fullerene C60, in 66% yield through ball milling of planar tetrabromomethylfluoranthene precursor under ambient conditions. Traditional solution and gas-phase synthetic pathways do not compete with the practicality and efficiency offered by the mechanochemical synthesis, which now opens up a new reaction space for inducing curvature at a molecular level.
Highlights
The transformation of planar aromatic molecules into π-extended non-planar structures is a challenging task and has not been realized by mechanochemistry before
Flash vacuum pyrolysis (FVP), in which molecules are subjected to high temperatures (500–1100 °C) in the gas-phase, is the most successful synthetic methodology to create non-planar molecules[1,2]
This feat of organic synthesis serves as an inspiration to explore new methods that can twist aromatic molecules and create new covalent bonds to lock the curved molecular geometry
Summary
An aldol condensation of 2 leads to 3, followed by a Diels-Alder reaction to yield
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