A stable open-shell peri-hexacene with remarkable diradical character
Abstract [n]Peri-acenes ([n]PA) have attracted great interest as promising candidates for nanoelectronics and spintronics. However, the synthesis of large [n]PA (n > 4) is extremely challenging due to their intrinsic open-shell radical character and high reactivity. Herein, we report the successf...
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55556-5 |
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| author | Jinji Zhang Xiaojing Fang Weiwei Niu Yiming Yu Yanlin Hu Jiawen Sun Ying Xu Zhihua Zhou Heyuan Liu Xiaonan Fan Baishu Zheng Qing Jiang Guangwu Li Wangdong Zeng |
| author_facet | Jinji Zhang Xiaojing Fang Weiwei Niu Yiming Yu Yanlin Hu Jiawen Sun Ying Xu Zhihua Zhou Heyuan Liu Xiaonan Fan Baishu Zheng Qing Jiang Guangwu Li Wangdong Zeng |
| author_sort | Jinji Zhang |
| collection | DOAJ |
| description | Abstract [n]Peri-acenes ([n]PA) have attracted great interest as promising candidates for nanoelectronics and spintronics. However, the synthesis of large [n]PA (n > 4) is extremely challenging due to their intrinsic open-shell radical character and high reactivity. Herein, we report the successful synthesis and isolation of a derivative (1) of peri-hexacene in crystalline form. The structure of 1 is unequivocally confirmed by X-ray crystallographic analysis. Its ground state, aromaticity and photophysical properties are systematically studied by both experimental methods and theoretical calculations. Although the parent peri-hexacene is calculated to have a very large diradical character (y 0 = 94.5%), 1 shows reasonable stability (t 1/2 = 24 h under ambient conditions) due to the kinetic blocking. 1 exhibits an open-shell singlet ground state with a small singlet-triplet energy gap (−1.33 kcal/mol from SQUID measurements). 1 has also a narrow HOMO-LUMO energy gap (1.05 eV) and displays amphoteric redox behavior. This work opens new avenues for the design and synthesis of stable zigzag-edged graphene-like molecules with significant diradical character. |
| format | Article |
| id | doaj-art-1d0ae397064545deb35b4d8a0890e29f |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-1d0ae397064545deb35b4d8a0890e29f2025-01-05T12:37:17ZengNature PortfolioNature Communications2041-17232025-01-011611910.1038/s41467-024-55556-5A stable open-shell peri-hexacene with remarkable diradical characterJinji Zhang0Xiaojing Fang1Weiwei Niu2Yiming Yu3Yanlin Hu4Jiawen Sun5Ying Xu6Zhihua Zhou7Heyuan Liu8Xiaonan Fan9Baishu Zheng10Qing Jiang11Guangwu Li12Wangdong Zeng13School of Materials Science and Engineering, Hunan University of Science and TechnologySchool of Materials Science and Engineering, Hunan University of Science and TechnologyCenter of Single-Molecule Sciences, Institute of Modern Optics, Tianjin Key Laboratory of Micro-Scale Optical Information Science and Technology, College of Electronic Information and Optical Engineering, Nankai UniversitySchool of Materials Science and Engineering, Hunan University of Science and TechnologySchool of Materials Science and Engineering, Hunan University of Science and TechnologySchool of Materials Science and Engineering, Hunan University of Science and TechnologySchool of Materials Science and Engineering, Hunan University of Science and TechnologyKey Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and TechnologySchool of Materials Science and Engineering, China University of Petroleum (East China)School of Materials Science and Engineering, China University of Petroleum (East China)Key Laboratory of Theoretical Organic Chemistry and Function Molecule of Ministry of Education, Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and TechnologyCollege of Chemistry and Bioengineering, Hunan University of Science and EngineeringCenter of Single-Molecule Sciences, Institute of Modern Optics, Tianjin Key Laboratory of Micro-Scale Optical Information Science and Technology, College of Electronic Information and Optical Engineering, Nankai UniversitySchool of Materials Science and Engineering, Hunan University of Science and TechnologyAbstract [n]Peri-acenes ([n]PA) have attracted great interest as promising candidates for nanoelectronics and spintronics. However, the synthesis of large [n]PA (n > 4) is extremely challenging due to their intrinsic open-shell radical character and high reactivity. Herein, we report the successful synthesis and isolation of a derivative (1) of peri-hexacene in crystalline form. The structure of 1 is unequivocally confirmed by X-ray crystallographic analysis. Its ground state, aromaticity and photophysical properties are systematically studied by both experimental methods and theoretical calculations. Although the parent peri-hexacene is calculated to have a very large diradical character (y 0 = 94.5%), 1 shows reasonable stability (t 1/2 = 24 h under ambient conditions) due to the kinetic blocking. 1 exhibits an open-shell singlet ground state with a small singlet-triplet energy gap (−1.33 kcal/mol from SQUID measurements). 1 has also a narrow HOMO-LUMO energy gap (1.05 eV) and displays amphoteric redox behavior. This work opens new avenues for the design and synthesis of stable zigzag-edged graphene-like molecules with significant diradical character.https://doi.org/10.1038/s41467-024-55556-5 |
| spellingShingle | Jinji Zhang Xiaojing Fang Weiwei Niu Yiming Yu Yanlin Hu Jiawen Sun Ying Xu Zhihua Zhou Heyuan Liu Xiaonan Fan Baishu Zheng Qing Jiang Guangwu Li Wangdong Zeng A stable open-shell peri-hexacene with remarkable diradical character Nature Communications |
| title | A stable open-shell peri-hexacene with remarkable diradical character |
| title_full | A stable open-shell peri-hexacene with remarkable diradical character |
| title_fullStr | A stable open-shell peri-hexacene with remarkable diradical character |
| title_full_unstemmed | A stable open-shell peri-hexacene with remarkable diradical character |
| title_short | A stable open-shell peri-hexacene with remarkable diradical character |
| title_sort | stable open shell peri hexacene with remarkable diradical character |
| url | https://doi.org/10.1038/s41467-024-55556-5 |
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