Dearomatizing [4+1] Spiroannulation of Naphthols: Discovery of Thermally Activated Delayed Fluorescent Materials

Disclosed here is a palladium-catalyzed direct [4+1] spiroannulation of ortho-C-H bonds of naphthols with cyclic diaryliodonium salts to construct spirofluorenyl naphthalenones (SFNP) under mild reaction conditions. This spiroannulation directly transforms the hydroxy group into a carbonyl group, and also tolerates reactive functional groups such as the halo groups, which provide an opportunity to rapidly assemble structurally new thermally activated delayed fluorescent (TADF) materials that feature a carbonyl group with an adjacent spirofluorenyl unit as the acceptor. As an illustrated example, the OLED device utilizing the assembled DMAC-SFNP as the host material exhibits a low turn-on voltage of 2.5 V and an ultra-high external quantum efficiency of 32.2 %. This work provides inspiration for structurally new TADF materials, and also displays the potential of C-H activation as a synthetic strategy for the innovation of optoelectronic materials.

Automated summary

This paper presents a palladium-catalyzed direct [4+1] spiroannulation reaction to construct spirofluorenyl naphthalenones under mild conditions, providing a potential synthetic strategy for the innovation of optoelectronic materials. The study also demonstrates the tolerance of reactive functional groups and the potential for rapidly assembling structurally new TADF materials.