Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole
Silole- and phosphole-containing polycyclic aromatic compounds have attracted significant attention in the field of organic functional materials. The structure of the aromatic units has great impact on the photophysical properties of the resulting silole- and phosphole-containing polycyclic aromatic...
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2024-09-01
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| author | Suzuho Morishita Chikara Hayasaka Keiichi Noguchi Koji Nakano |
| author_facet | Suzuho Morishita Chikara Hayasaka Keiichi Noguchi Koji Nakano |
| author_sort | Suzuho Morishita |
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| description | Silole- and phosphole-containing polycyclic aromatic compounds have attracted significant attention in the field of organic functional materials. The structure of the aromatic units has great impact on the photophysical properties of the resulting silole- and phosphole-containing polycyclic aromatic compounds. Here, dibenzo-fused naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole (NDS) and naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole (NDP), where a naphthalene unit is arranged between two silole and phosphole units, respectively, were designed and synthesized. The solid-state structures of them were confirmed by X-ray crystallographic analysis. The photophysical properties were evaluated by UV−vis absorption and photoluminescence spectroscopies and compared with those of their related compounds, such as dibenzo-fused silolo[3,2-<i>b</i>]silole and benzo[1,2-<i>b</i>:4,5-<i>b</i>′]disilole, ever reported. The longest wavelength absorption band of a series of silole-fused compounds was found to be red-shifted in the order benzo[1,2-<i>b</i>:4,5-<i>b</i>′]disilole < NDS < silolo[3,2-<i>b</i>]silole derivatives. For a series of phosphole-fused compounds, π-extension from phospholo[3,2-<i>b</i>]phosphole to NDP derivatives induces the lower absorption coefficient of the longest wavelength absorption band and the red-shift of the second longest wavelength absorption band. Both NDS and NDP exhibit much lower fluorescence quantum yields than their related compounds. |
| format | Article |
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| publishDate | 2024-09-01 |
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| series | Molecules |
| spelling | doaj-art-ab55225f2f7443ce9bfad4b1148a89eb2025-08-20T01:55:42ZengMDPI AGMolecules1420-30492024-09-012918431310.3390/molecules29184313Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphospholeSuzuho Morishita0Chikara Hayasaka1Keiichi 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, JapanSilole- and phosphole-containing polycyclic aromatic compounds have attracted significant attention in the field of organic functional materials. The structure of the aromatic units has great impact on the photophysical properties of the resulting silole- and phosphole-containing polycyclic aromatic compounds. Here, dibenzo-fused naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole (NDS) and naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole (NDP), where a naphthalene unit is arranged between two silole and phosphole units, respectively, were designed and synthesized. The solid-state structures of them were confirmed by X-ray crystallographic analysis. The photophysical properties were evaluated by UV−vis absorption and photoluminescence spectroscopies and compared with those of their related compounds, such as dibenzo-fused silolo[3,2-<i>b</i>]silole and benzo[1,2-<i>b</i>:4,5-<i>b</i>′]disilole, ever reported. The longest wavelength absorption band of a series of silole-fused compounds was found to be red-shifted in the order benzo[1,2-<i>b</i>:4,5-<i>b</i>′]disilole < NDS < silolo[3,2-<i>b</i>]silole derivatives. For a series of phosphole-fused compounds, π-extension from phospholo[3,2-<i>b</i>]phosphole to NDP derivatives induces the lower absorption coefficient of the longest wavelength absorption band and the red-shift of the second longest wavelength absorption band. Both NDS and NDP exhibit much lower fluorescence quantum yields than their related compounds.https://www.mdpi.com/1420-3049/29/18/4313silolephospholeπ-conjugated compoundUV–vis absorption propertyphotoluminescence |
| spellingShingle | Suzuho Morishita Chikara Hayasaka Keiichi Noguchi Koji Nakano Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole Molecules silole phosphole π-conjugated compound UV–vis absorption property photoluminescence |
| title | Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole |
| title_full | Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole |
| title_fullStr | Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole |
| title_full_unstemmed | Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole |
| title_short | Synthesis and Properties of Dibenzo-Fused Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]disilole and Naphtho[2,3-<i>b</i>:6,7-<i>b</i>′]diphosphole |
| title_sort | synthesis and properties of dibenzo fused naphtho 2 3 i b i 6 7 i b i disilole and naphtho 2 3 i b i 6 7 i b i diphosphole |
| topic | silole phosphole π-conjugated compound UV–vis absorption property photoluminescence |
| url | https://www.mdpi.com/1420-3049/29/18/4313 |
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