Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives
A novel series of D−A−D-type 9-phenyl-9-phosphafluorene oxide (PhFlOP) derivatives was prepared and is reported herein. The synthetic protocol involved 5 steps from commercially available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2024-12-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.20.274 |
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| author | Shuxian Qiu Duan Dong Jiahui Li Huiting Wen Jinpeng Li Yu Yang Shengxian Zhai Xingyuan Gao |
| author_facet | Shuxian Qiu Duan Dong Jiahui Li Huiting Wen Jinpeng Li Yu Yang Shengxian Zhai Xingyuan Gao |
| author_sort | Shuxian Qiu |
| collection | DOAJ |
| description | A novel series of D−A−D-type 9-phenyl-9-phosphafluorene oxide (PhFlOP) derivatives was prepared and is reported herein. The synthetic protocol involved 5 steps from commercially available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final Cs2CO3-facilitated nucleophilic substitution (77–91% yield). The characterization data obtained from IR and NMR spectroscopy (1H, 13C, 19F, and 31P) as well as HRMS spectrometry were in full agreement with the expected structures, and single-crystal X-ray diffraction analysis was conducted to confirm the structure of compound 7-H. Moreover, the photophysical properties of these PhFlOP derivatives were determined by UV–vis absorption and photoluminescence studies, revealing that their photophysical behavior can be affected by the different substituents in the donor carbazole group. |
| format | Article |
| id | doaj-art-7d87cf2c1923453f844df19f2bad3d85 |
| institution | Kabale University |
| issn | 1860-5397 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj-art-7d87cf2c1923453f844df19f2bad3d852025-01-06T12:27:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972024-12-012013299330510.3762/bjoc.20.2741860-5397-20-274Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivativesShuxian Qiu0Duan Dong1Jiahui Li2Huiting Wen3Jinpeng Li4Yu Yang5Shengxian Zhai6Xingyuan Gao7College of Chemistry and Material Science, Guangdong University of Education, Guangzhou 510303, China College of Chemistry and Chemical Engineering, Tarim University, Aral City 843300, China College of Chemistry and Material Science, Guangdong University of Education, Guangzhou 510303, China College of Chemistry & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, China College of Chemistry and Material Science, Guangdong University of Education, Guangzhou 510303, China College of Chemistry & Environmental Engineering, Anyang Institute of Technology, Anyang 455000, China College of Chemistry and Chemical Engineering, Tarim University, Aral City 843300, China College of Chemistry and Material Science, Guangdong University of Education, Guangzhou 510303, China A novel series of D−A−D-type 9-phenyl-9-phosphafluorene oxide (PhFlOP) derivatives was prepared and is reported herein. The synthetic protocol involved 5 steps from commercially available 2-bromo-4-fluoro-1-nitrobenzene, featuring a noble-metal-free system, mild reaction conditions, and a good yield, especially for the final Cs2CO3-facilitated nucleophilic substitution (77–91% yield). The characterization data obtained from IR and NMR spectroscopy (1H, 13C, 19F, and 31P) as well as HRMS spectrometry were in full agreement with the expected structures, and single-crystal X-ray diffraction analysis was conducted to confirm the structure of compound 7-H. Moreover, the photophysical properties of these PhFlOP derivatives were determined by UV–vis absorption and photoluminescence studies, revealing that their photophysical behavior can be affected by the different substituents in the donor carbazole group.https://doi.org/10.3762/bjoc.20.274carbazoled−a−d typenoble-metal-free system9‑phenyl-9-phosphafluorene oxidephotophysical properties |
| spellingShingle | Shuxian Qiu Duan Dong Jiahui Li Huiting Wen Jinpeng Li Yu Yang Shengxian Zhai Xingyuan Gao Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives Beilstein Journal of Organic Chemistry carbazole d−a−d type noble-metal-free system 9‑phenyl-9-phosphafluorene oxide photophysical properties |
| title | Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives |
| title_full | Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives |
| title_fullStr | Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives |
| title_full_unstemmed | Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives |
| title_short | Synthesis, characterization, and photophysical properties of novel 9‑phenyl-9-phosphafluorene oxide derivatives |
| title_sort | synthesis characterization and photophysical properties of novel 9 phenyl 9 phosphafluorene oxide derivatives |
| topic | carbazole d−a−d type noble-metal-free system 9‑phenyl-9-phosphafluorene oxide photophysical properties |
| url | https://doi.org/10.3762/bjoc.20.274 |
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