Neutral Möbius [5]helicene-embedded Cycloparaphenylene Nanohoops: Synthesis, [4n]Möbius Topology and Hückel Aromaticity
The relationship between Möbius topology and aromaticity and topological chirality is still elusive to date, which is, to a large extent, due to the related synthetic challenges and, further, the scarcity in both the quantity and the diversity of the con-structed Möbius systems. In this work, we reported the synthesis of [4n]Möbius conjugated all-carbon nanohoops ([5]H-[7,8]CPPs) by utilizing a [5]helicene unit as a hidden writhe and a masked aromatic unit to overcome the strain inherited from Möbius topology. X-ray analysis revealed that [5]H-[7,8]CPPs contain a [5]helicene moiety and an oligoparaphenylene unit, and display a Möbius topology. Photophysical investigations demonstrated that [5]H-[7,8]CPPs exhibited moderately high fluorescence quantum yields, which are significantly higher than those of pristine [5]helicene and [7,8]CPPs. Chiropti-cal studies revealed that [5]H-[7,8]CPPs displayed an obvious Cotton effect in circular dichroism and bright circularly polar-ized luminescence, indicating that the chirality of [5]helicene was efficiently transferred to the overall carbon nanohoops. Importantly, theoretical investigations reveal that, though possessing a 4n π-electron array, such all-carbon nanohoops are fully conjugated systems with Hückel aromaticity. The results may help us to better understand the relationship between Möbius topology and aromaticity..
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Preprint| Erscheinungsjahr: |
2024 |
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| Erschienen: |
2024 |
| Enthalten in: |
chemRxiv.org - (2024) vom: 29. Jan. Zur Gesamtaufnahme - year:2024 |
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| Sprache: |
Englisch |
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| Beteiligte Personen: |
Yang, Huiji [VerfasserIn] |
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| Links: |
Volltext [kostenfrei] |
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| doi: |
10.26434/chemrxiv-2024-vxf63 |
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| PPN (Katalog-ID): |
XCH042320577 |
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| 245 | 1 | 0 | |a Neutral Möbius [5]helicene-embedded Cycloparaphenylene Nanohoops: Synthesis, [4n]Möbius Topology and Hückel Aromaticity |
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| 520 | |a The relationship between Möbius topology and aromaticity and topological chirality is still elusive to date, which is, to a large extent, due to the related synthetic challenges and, further, the scarcity in both the quantity and the diversity of the con-structed Möbius systems. In this work, we reported the synthesis of [4n]Möbius conjugated all-carbon nanohoops ([5]H-[7,8]CPPs) by utilizing a [5]helicene unit as a hidden writhe and a masked aromatic unit to overcome the strain inherited from Möbius topology. X-ray analysis revealed that [5]H-[7,8]CPPs contain a [5]helicene moiety and an oligoparaphenylene unit, and display a Möbius topology. Photophysical investigations demonstrated that [5]H-[7,8]CPPs exhibited moderately high fluorescence quantum yields, which are significantly higher than those of pristine [5]helicene and [7,8]CPPs. Chiropti-cal studies revealed that [5]H-[7,8]CPPs displayed an obvious Cotton effect in circular dichroism and bright circularly polar-ized luminescence, indicating that the chirality of [5]helicene was efficiently transferred to the overall carbon nanohoops. Importantly, theoretical investigations reveal that, though possessing a 4n π-electron array, such all-carbon nanohoops are fully conjugated systems with Hückel aromaticity. The results may help us to better understand the relationship between Möbius topology and aromaticity. | ||
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| 700 | 1 | |a Guo, Shengzhu |4 aut | |
| 700 | 1 | |a Guo, Weijie |4 aut | |
| 700 | 1 | |a Liu, Xiaoyu |4 aut | |
| 700 | 1 | |a He, Jing |4 aut | |
| 700 | 1 | |a Fan, Yanqing |4 aut | |
| 700 | 1 | |a Lian, Zhe |4 aut | |
| 700 | 1 | |a Li, Xiaonan |4 aut | |
| 700 | 1 | |a Wang, Ying |4 aut | |
| 700 | 1 | |a Jiang, Hua |0 (orcid)0000-0002-9917-2683 |4 aut | |
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