Columnar Stacking of Partially Fluorinated [4]Helicenes: C-Hâ
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F Interactions Change the Stacking Orientation.
Chem Asian J
; 15(8): 1330-1338, 2020 Apr 17.
Article
em En
| MEDLINE
| ID: mdl-32083804
ABSTRACT
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-Hâ
â
â
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.
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Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article