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高效发光体：通过一锅法合成含C-O-P到C-P(═O)重排的10-(二苯基磷酰基)-蒽

High-Efficiency Light Emitters: 10-(Diphenylphosphoryl)-anthracenes from One-Pot Synthesis Including C-O-P to C-P(═O) Rearrangement.

作者信息

Vivek Vivek, Koprowski Marek, Różycka-Sokołowska Ewa, Turek Marika, Dudziński Bogdan, Owsianik Krzysztof, Knopik Łucja, Bałczewski Piotr

机构信息

Division of Organic Chemistry, Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, Łódź 90-363, Poland.

The Bio-Med-Chem Doctoral School of the University of Łódź and Łódź Institutes of the Polish Academy of Sciences, University of Łódź, Matejki 21/23, Łódź 90-237, Poland.

出版信息

J Org Chem. 2025 Apr 4;90(13):4580-4590. doi: 10.1021/acs.joc.4c03139. Epub 2025 Mar 25.

DOI:10.1021/acs.joc.4c03139
PMID:40133206
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11976837/
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, MeO, OCHO) 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 PhP═O group, and the aggregation effect in solid on the photophysical properties, were also explored.

摘要

我们报道了一种一锅法合成10-(二苯基磷酰基)蒽的方法，其侧环上带有供体-受体基团（F、Br、CN、CF、MeO、OCHO）的罕见多取代产物，产率为24-60%。在三甲基甲磺酸镱（TMSOTf）催化下，该过程涉及亚膦酸酯到氧化膦的重排和环化。这些发光体在溶液和固态中均表现出高达95%的优异光致发光量子产率。还探索了合成后蒽的功能化以及取代基的光电效应，特别是PhP═O基团，以及固态中的聚集效应对光物理性质的影响。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/eb77e7fb1b98/jo4c03139_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/87bf73bd87ff/jo4c03139_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/7ff6367e093e/jo4c03139_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/ff0d9b114025/jo4c03139_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/6be6d51851b7/jo4c03139_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/43b881673be5/jo4c03139_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/ca5a674f6355/jo4c03139_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/1d110afb808e/jo4c03139_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/2f0f6ac4aa76/jo4c03139_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/eb77e7fb1b98/jo4c03139_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/87bf73bd87ff/jo4c03139_0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/7ff6367e093e/jo4c03139_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/ff0d9b114025/jo4c03139_0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/6be6d51851b7/jo4c03139_0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/43b881673be5/jo4c03139_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/ca5a674f6355/jo4c03139_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/1d110afb808e/jo4c03139_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/2f0f6ac4aa76/jo4c03139_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/27f0/11976837/eb77e7fb1b98/jo4c03139_0006.jpg

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