Aroyl-S,N-Ketene Acetals: Luminous Renaissance of a Class of Heterocyclic Compounds

Aroyl-S,N-ketene acetals represent a peculiar class of heterocyclic merocyanines, compounds bearing pronounced and rather short dipoles with great push-pull characteristics that define their rich properties. They are accessible via a wide array of synthetic concepts and procedures, ranging from addition-elimination and condensation procedures up to rearrangement and metal-mediated reactions. With our work from 2020, aroyl-S,N-ketene acetals have been identified as powerful and promising dyes with pronounced and vastly tunable solid-state emission and aggregation-induced emission properties. One characteristic trademark of this class of dye molecules is the level of control that could be exerted, and which was thoroughly explored. Based on these results, the field was opened to extend the system to bi- and multichromophoric systems by the full toolkit of synthetic organic chemistry thus giving access to even more exciting properties and manifolded substance libraries capitalizing on the AIE properties. This review aims at outlining the reaction-based principles that allow for a swift and facile access to aroyl-S,N-ketene acetals, their methodical and structural evolution and the plethora of fluorescence and aggregation properties.

Automated summary

Aroyl-S,N-ketene acetals are a unique class of heterocyclic dyes with tunable solid-state emission and aggregation-induced emission properties. They can be synthesized using various methods and can be further expanded into systems with multiple chromophores.