Aza-tricycles containing a perfluoroalkyl group: synthesis, structure and fluorescence

Perfluoroalkyl-containing aza-tricycles have been prepared in one synthetic operation via an ambient light-promoted three-component reaction of beta-oxo esters, perfluoroalkyl iodide and DBU. Intramolecular C-F center dot center dot center dot O and double C-H center dot center dot center dot F weak interactions and intermolecular C-H center dot center dot center dot O and C-H center dot center dot center dot pi hydrogen bondings were observed partly due to the incorporation of the perfluoroalkyl group. The perfluoroalkylated non-planar aza-tricycles exhibit interesting room-temperature AIE fluorescence and acid-induced fluorescence enhancement characters.