Mechanochemical Transformation of Planar Polyarene to Curved Fused-Ring System: Solid-Phase Synthesis of Corannulene

08 January 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

This work demonstrates 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 15-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.

Keywords

mechanochemistry
Corannulene
cuved nanographenes
curved aromatics

Supplementary materials

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