The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings
The phosphole ring is known as a useful building block for constructing π-conjugated organic materials. Here, we report ladder-type benzophospholo[3,2-<i>b</i>]indole (BPI) derivatives where the phosphole and the pyrrole rings are directly fused. Compounds <b>8a</b>–<b>...
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MDPI AG
2023-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/29/1/38 |
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| author | Minh Anh Truong Suzuho Morishita Keiichi Noguchi Koji Nakano |
| author_facet | Minh Anh Truong Suzuho Morishita Keiichi Noguchi Koji Nakano |
| author_sort | Minh Anh Truong |
| collection | DOAJ |
| description | The phosphole ring is known as a useful building block for constructing π-conjugated organic materials. Here, we report ladder-type benzophospholo[3,2-<i>b</i>]indole (BPI) derivatives where the phosphole and the pyrrole rings are directly fused. Compounds <b>8a</b>–<b>8d</b> with different aryl groups on the phosphorous center were successfully synthesized, and the solid-state structure of <b>8a</b> was confirmed using X-ray crystallographic analysis. The BPIs exhibit relatively high fluorescence quantum yield (Φ 0.50−0.72) and demonstrate a larger Stokes shift compared with a series of benzophospholo[3,2-<i>b</i>]benzoheteroles. The benzophospholo[3,2-<i>b</i>]carbazole derivative <b>9</b>, which possesses a benzene ring between the phosphole and the pyrrole rings of the BPI, was also synthesized, and its solid-state structure was confirmed using X-ray crystallographic analysis. Compound <b>9</b> was found to show a smaller Stokes shift compared with the BPI. |
| first_indexed | 2024-03-08T15:01:01Z |
| format | Article |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-08T15:01:01Z |
| publishDate | 2023-12-01 |
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| series | Molecules |
| spelling | doaj.art-0b2b4569883545d4be0ce856cd0cb8642024-01-10T15:03:56ZengMDPI AGMolecules1420-30492023-12-012913810.3390/molecules29010038The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole RingsMinh Anh Truong0Suzuho Morishita1Keiichi Noguchi2Koji Nakano3Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, JapanInstrumentation Analysis Center, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, JapanDepartment of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, JapanThe phosphole ring is known as a useful building block for constructing π-conjugated organic materials. Here, we report ladder-type benzophospholo[3,2-<i>b</i>]indole (BPI) derivatives where the phosphole and the pyrrole rings are directly fused. Compounds <b>8a</b>–<b>8d</b> with different aryl groups on the phosphorous center were successfully synthesized, and the solid-state structure of <b>8a</b> was confirmed using X-ray crystallographic analysis. The BPIs exhibit relatively high fluorescence quantum yield (Φ 0.50−0.72) and demonstrate a larger Stokes shift compared with a series of benzophospholo[3,2-<i>b</i>]benzoheteroles. The benzophospholo[3,2-<i>b</i>]carbazole derivative <b>9</b>, which possesses a benzene ring between the phosphole and the pyrrole rings of the BPI, was also synthesized, and its solid-state structure was confirmed using X-ray crystallographic analysis. Compound <b>9</b> was found to show a smaller Stokes shift compared with the BPI.https://www.mdpi.com/1420-3049/29/1/38phospholepyrroleπ-conjugated compoundphotoluminescence |
| spellingShingle | Minh Anh Truong Suzuho Morishita Keiichi Noguchi Koji Nakano The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings Molecules phosphole pyrrole π-conjugated compound photoluminescence |
| title | The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings |
| title_full | The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings |
| title_fullStr | The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings |
| title_full_unstemmed | The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings |
| title_short | The Synthesis and Properties of Ladder-Type π-Conjugated Compounds with Pyrrole and Phosphole Rings |
| title_sort | synthesis and properties of ladder type π conjugated compounds with pyrrole and phosphole rings |
| topic | phosphole pyrrole π-conjugated compound photoluminescence |
| url | https://www.mdpi.com/1420-3049/29/1/38 |
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