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Dearomatizing [4+1] Spiroannulation of Naphthols: Discovery of Thermally Activated Delayed Fluorescent Materials
Author(s) -
Liang Wenbo,
Yang Yudong,
Yang Mufan,
Zhang Min,
Li Chengming,
Ran You,
Lan Jingbo,
Bin Zhengyang,
You Jingsong
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202012842
Subject(s) - fluorescence , acceptor , chemistry , palladium , combinatorial chemistry , photochemistry , functional group , catalysis , organic chemistry , polymer , physics , quantum mechanics , condensed matter physics
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.