Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties
Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-<i>b</i>][1]benzofuran-10,10′-indeno[1,2-<i>b</i>][1]benzothiophene]...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/16/5103 |
| _version_ | 1827599007472418816 |
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| author | Koji Nakano Ko Takase Keiichi Noguchi |
| author_facet | Koji Nakano Ko Takase Keiichi Noguchi |
| author_sort | Koji Nakano |
| collection | DOAJ |
| description | Spiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-<i>b</i>][1]benzofuran-10,10′-indeno[1,2-<i>b</i>][1]benzothiophene] as a new family of spiro-fused PACs that contains a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its <i>S</i>,<i>S</i>-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials. |
| first_indexed | 2024-03-09T04:03:04Z |
| format | Article |
| id | doaj.art-f38ebe1a0a4d4656b0f7c1e529c24f7c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:03:04Z |
| publishDate | 2022-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-f38ebe1a0a4d4656b0f7c1e529c24f7c2023-12-03T14:10:54ZengMDPI AGMolecules1420-30492022-08-012716510310.3390/molecules27165103Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical PropertiesKoji Nakano0Ko Takase1Keiichi Noguchi2Department 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, JapanSpiro-fused polycyclic aromatic compounds (PACs) have received growing interest as rigid chiral scaffolds. However, furan-containing spiro-fused PACs have been quite limited. Here, we design spiro[indeno[1,2-<i>b</i>][1]benzofuran-10,10′-indeno[1,2-<i>b</i>][1]benzothiophene] as a new family of spiro-fused PACs that contains a furan unit. The compound was successfully synthesized in enantiopure form and also transformed to its <i>S</i>,<i>S</i>-dioxide derivative and the pyrrole-containing analog via aromatic metamorphosis. The absorption and emission properties of the obtained furan-containing chiral spiro-fused PACs are apparently different from those of their thiophene analogs that have been reported, owing to the increased electron-richness of furan compared to thiophene. All of the furan-containing chiral spiro-fused PACs were found to be circularly polarized luminescent materials.https://www.mdpi.com/1420-3049/27/16/5103spiro π-conjugated compoundchiral compoundthiophenefuranpyrrolenucleophilic aromatic substitution |
| spellingShingle | Koji Nakano Ko Takase Keiichi Noguchi Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties Molecules spiro π-conjugated compound chiral compound thiophene furan pyrrole nucleophilic aromatic substitution |
| title | Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties |
| title_full | Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties |
| title_fullStr | Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties |
| title_full_unstemmed | Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties |
| title_short | Furan-Containing Chiral Spiro-Fused Polycyclic Aromatic Compounds: Synthesis and Photophysical Properties |
| title_sort | furan containing chiral spiro fused polycyclic aromatic compounds synthesis and photophysical properties |
| topic | spiro π-conjugated compound chiral compound thiophene furan pyrrole nucleophilic aromatic substitution |
| url | https://www.mdpi.com/1420-3049/27/16/5103 |
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