High-EfficiencyLightEmitters: 10-(Diphenylphosphoryl)-anthracenesfrom One-Pot Synthesis Including C–O–P to C–P(O)Rearrangement

We report a one-pot synthesis of 10-(diphenylphosphoryl)-anthracenes, featuring a rare multisubstitution on flanking rings with donor–acceptor groups (F, Br, CN, CF<sub>3</sub>, MeO, OCH<sub>2</sub>O) 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 Ph<sub>2</sub>PO group, and the aggregation effect in solid on the photophysical properties, were also explored.

Publication Details

Journal
Figshare
Published
2025-03-26
DOI
https://doi.org/10.1021/acs.joc.4c03139.s001
Primary Topic
Synthesis and characterization of novel inorganic/organometallic compounds
Type
article
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High-EfficiencyLightEmitters: 10-(Diphenylphosphoryl)-anthracenesfrom One-Pot Synthesis Including C–O–P to C–P(O)Rearrangement

Figshare
Synthesis and characterization of novel inorganic/organometallic compounds
article

High-EfficiencyLightEmitters: 10-(Diphenylphosphoryl)-anthracenesfrom One-Pot Synthesis Including C–O–P to C–P(O)Rearrangement

article en

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, CF<sub>3</sub>, MeO, OCH<sub>2</sub>O) 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 Ph<sub>2</sub>PO group, and the aggregation effect in solid on the photophysical properties, were also explored.

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Openalex Percentile: Top 63%
Synthesis and characterization of novel inorganic/organometallic compounds
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High-EfficiencyLightEmitters: 10-(Diphenylphosphoryl)-anthracenesfrom One-Pot Synthesis Including C–O–P to C–P(O)Rearrangement · Figshare (2025) | TGRS Research Map | TGRS