ja974072a_si_002.pdf (714.49 kB)
Phenyl−Perfluorophenyl Stacking Interactions: Topochemical [2+2] Photodimerization and Photopolymerization of Olefinic Compounds
journal contribution
posted on 1998-04-02, 00:00 authored by Geoffrey W. Coates, Alex R. Dunn, Lawrence M. Henling, Joseph W. Ziller, Emil B. Lobkovsky, Robert H. GrubbsThe 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.
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photoproductgeneralitysupramolecular synthoncocrystalline materialsphotochemicallyanalysisPhotodimerizationolefinic precursorsnoncovalent interactionPhenylmonoolefinreactivitydiolefinstereochemistryInteractionPhotopolymerizationperfluorophenyl groupsphotoactive crystalsStackingOlefinic CompoundsTopochemical
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