High-Efficiency Light Emitters: 10-(Diphenylphosphoryl)-anthracenes from 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.
Authors
- Vivek Vivek (ORCID: https://orcid.org/0000-0003-1058-8744)
- Marika Turek (ORCID: https://orcid.org/0000-0002-7978-8384)
- Piotr Bałczewski (ORCID: https://orcid.org/0000-0001-5981-551X)
- Łucja Knopik (ORCID: https://orcid.org/0000-0001-7351-6997)
- Bogdan Dudziński (ORCID: https://orcid.org/0000-0002-5648-998X)
- Ewa Różycka‐Sokołowska (ORCID: https://orcid.org/0000-0001-5980-6939)
- Marek Koprowski (ORCID: https://orcid.org/0000-0003-0122-1326)
- Krzysztof Owsianik (ORCID: https://orcid.org/0000-0002-9053-3315)
Institutions
- Jan Długosz University (PL)
- University of Łódź (PL)
- Centrum Badań Molekularnych i Makromolekularnych Polskiej Akademii Nauk (PL)
- Polish Academy of Sciences (PL)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-03-25
- DOI
- https://doi.org/10.1021/acs.joc.4c03139
- Citations
- 1
- Primary Topic
- Luminescence and Fluorescent Materials
- Type
- article
- Field-Weighted Citation Impact
- 0.52
Funders
- Narodowe Centrum Nauki