Stereoselective and quantitative [2 + 2] photodimerization of a symmetrical octafluoro stilbene in the solid state: Face-to-face stacking of the fluorinated rings in trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene

•Stereoselective and quantitative [2 + 2] photodimerization.•Solid-state synthesis of fluoroarene.•Polyfluorophenyl interactions.

The symmetrical octafluoro stilbene trans-1,2-bis(2,3,5,6-tetrafluorophenyl)ethylene (1) undergoes a stereoselective and quantitative [2 + 2] photodimerization in the solid state. The olefin self-assembles via C-H⋯F and face-to-face interactions of the fluorinated phenyl rings into a geometry for a topochemical photodimerization. The crystal structure and stereochemistry of the photoproduct rctt-1,2,3,4-tetrakis(2,3,5,6-tetrafluorophenyl)cyclobutane (2) has been determined.

Graphical abstractThe symmetrical octafluoro stilbene undergoes a stereoselective and quantitative [2 + 2] photodimerization in the solid state. CH⋯F interactions and face-to-face stacking dominate the self-assembly of the alkene in the solid. The resulting cyclobutane possesses four polyfluoro phenyl groups in a rctt-configuration.Figure optionsDownload full-size imageDownload as PowerPoint slide