Phenyl−Perfluorophenyl Stacking Interactions:  Topochemical [2+2] Photodimerization and Photopolymerization of Olefinic Compounds Geoffrey W. Coates Alex R. Dunn Lawrence M. Henling Joseph W. Ziller Emil B. Lobkovsky Robert H. Grubbs 10.1021/ja974072a.s002 https://acs.figshare.com/articles/journal_contribution/Phenyl_Perfluorophenyl_Stacking_Interactions_Topochemical_2_2_Photodimerization_and_Photopolymerization_of_Olefinic_Compounds/3668640 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. 1998-04-02 00:00:00 photoproduct generality supramolecular synthon cocrystalline materials photochemically analysis Photodimerization olefinic precursors noncovalent interaction Phenyl monoolefin reactivity diolefin stereochemistry Interaction Photopolymerization perfluorophenyl groups photoactive crystals Stacking Olefinic Compounds Topochemical