The face-to-face stacking interaction between phenyl and
perfluorophenyl groups is emerging as a
common noncovalent interaction. To explore the generality of this
supramolecular synthon, the solid-state
packing structure and reactivity of several monoolefins and diolefins
substituted with phenyl and perfluorophenyl
groups was investigated. Of the seven crystalline or cocrystalline
materials investigated, six were found to
undergo a photochemically induced [2+2] reaction in the solid
state. By determining the stereochemistry of
the photoproduct and/or X-ray structural analysis of the olefinic
precursors, the stacked interaction between
phenyl and perfluorophenyl groups in the photoactive crystals were
revealed.
A stabilization of the liquid-crystalline mesophase and thus an enlarged temperature range of the mesogenic phase is achieved by adding perfluorotriphenylene to a chiral liquid-crystalline triphenylene. This mesophase is based on 1:1 perfluoroarene-arene interactions (see picture). In a polymer with triphenylenes as mesogens in the side chains, the addition of perfluorotriphenylene led to crystallization.
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