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High-Efficiency Light Emitters: 10-(Diphenylphosphoryl)-anthracenes from One-Pot Synthesis Including C-O-P to C-P(═O)
Vivek Vivek1,2, Marek Koprowski1, Ewa Różycka-Sokołowska3
1Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź 90-363, Poland.
Abstract:
We report a one-pot synthesis of 10-(diphenylphosphoryl)-anthracenes, featuring a rare multisubstitution on flanking rings with donor-acceptor groups (F, Br, CN, CF3, MeO, OCH2O) in 24-60% yields. Catalyzed by TMSOTf, the process involves a phosphinite-to-phosphine oxide rearrangement and cyclization. These emitters exhibit excellent photoluminescence quantum yields of up to 95% in both solution and solid states. Postsynthetic anthracene functionalization as well as the optoelectronic effect of substituents, particularly the Ph2P═O group, and the aggregation effect in solid on the photophysical properties, were also explored.
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