Carbon origami via an alumina-assisted cyclodehydrofluorination strategy

Abstract

The synthesis of pristine non-planar nanographenes (NGs) via a cyclodehydrofluorination strategy is reported and the creation of highly strained systems via alumina-assisted C−F bond activation is shown. Steric hindrance could execute an alternative coupling program leading to rare octagon formation offering access to elusive non-classical NGs. The combination of two alternative ways of folding could lead to the formation of various 3D NG objects, resembling the Japanese art of origami. The power of the presented “origami” approach is proved by the assembly of 12 challenging nanographenes that are π-isoelectronic to planar hexabenzocoronene but forced out of planarity.