132445-88-6Relevant articles and documents
Columnar Stacking of Partially Fluorinated [4]Helicenes: C?H???F Interactions Change the Stacking Orientation
Fujiwara, Wataru,Katagiri, Hiroshi,Murase, Takashi,Suzuki, Risa,Uziie, Yuto
supporting information, (2020/04/15)
The partial fluorination of polycyclic aromatic hydrocarbons often produces a layered crystal packing, where fluorinated aromatic surfaces are stacked over nonfluorinated aromatic surfaces. Herein, we report the synthesis and crystal packing of partially fluorinated [4]helicenes with steric congestion resulting from H and F atoms in the fjord region. F6-[4]Helicene forms head-to-tail columnar stacks consisting of an alternate arrangement of perfluorinated and nonfluorinated naphthalene moieties. With decreasing fluorine content, aromatic stacking switched from arene?fluoroarene (ArH?ArF) hetero-stacking to ArH?ArH/ArF?ArF homo-stacking with the help of intermolecular C?H???F contacts in the fjord region. As a result, head-to-head columnar stacks appear. Therefore, the conventional ArH?ArF stacking motif is not always applicable to Fn-[4]helicenes with twisted π-surfaces.