Chiral Carbon Nanorings : Synthesis, Properties and Hierarchical Self‐assembly of Chiral Ternary Complexes Featuring a Narcissistic Chiral Self‐Recognition for Chiral Amines
Abstract We report the synthesis and chiroptical properties of novel chiral carbon nanorings S p‐/ R p‐[12]PCPP containing a planar chiral [2.2]PCP unit, and demonstrate that S p‐/ R p‐[12]PCPP can not only host crown ether 18‐Crown‐6 to form ring‐in‐ring complexes with a binding constant 3.35×103 M−1, but also accommodate the complexes of 18‐Crown‐6 and S/R‐protonated amines to form homochiral SS p‐/ R@ R p‐ and heterochiral S@ R p‐/ R@ S p‐ ternary complexes, displaying significantly larger binding constants of up to 3.31×105 M−1 depending on the chiral guests. Importantly, homochiral S@ S p‐/ R@ R p‐ ternary complexes exhibit an enhanced CD signal, while the heterochiral S@ R p‐/ R@ S p‐ ones have a constant CD signal compared with the chiral carbon nanorings, respectively, which suggests that homochiral S@ S p‐/ R@ R p‐ ternary complexes display a highly narcissistic chiral self‐recognition for S/ R‐protonated chiral amines, respectively. Finally, the chiral ternary complexes can be further applied to determine the ee values of chiral guests. The findings highlight a new application of carbon nanorings in supramolecular sensors, beyond the common recognition of π‐conjugated molecules..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2023 |
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| Erschienen: |
2023 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:62 |
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| Enthalten in: |
Angewandte Chemie International Edition - 62(2023), 28 |
| Beteiligte Personen: |
Fan, Yanqing [VerfasserIn] |
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| Anmerkungen: |
© 2023 Wiley‐VCH GmbH |
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| Umfang: |
7 |
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| doi: |
10.1002/anie.202304623 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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WLY01503075X |
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| 245 | 1 | 0 | |a Chiral Carbon Nanorings |b Synthesis, Properties and Hierarchical Self‐assembly of Chiral Ternary Complexes Featuring a Narcissistic Chiral Self‐Recognition for Chiral Amines |
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| 520 | |a Abstract We report the synthesis and chiroptical properties of novel chiral carbon nanorings S p‐/ R p‐[12]PCPP containing a planar chiral [2.2]PCP unit, and demonstrate that S p‐/ R p‐[12]PCPP can not only host crown ether 18‐Crown‐6 to form ring‐in‐ring complexes with a binding constant 3.35×103 M−1, but also accommodate the complexes of 18‐Crown‐6 and S/R‐protonated amines to form homochiral SS p‐/ R@ R p‐ and heterochiral S@ R p‐/ R@ S p‐ ternary complexes, displaying significantly larger binding constants of up to 3.31×105 M−1 depending on the chiral guests. Importantly, homochiral S@ S p‐/ R@ R p‐ ternary complexes exhibit an enhanced CD signal, while the heterochiral S@ R p‐/ R@ S p‐ ones have a constant CD signal compared with the chiral carbon nanorings, respectively, which suggests that homochiral S@ S p‐/ R@ R p‐ ternary complexes display a highly narcissistic chiral self‐recognition for S/ R‐protonated chiral amines, respectively. Finally, the chiral ternary complexes can be further applied to determine the ee values of chiral guests. The findings highlight a new application of carbon nanorings in supramolecular sensors, beyond the common recognition of π‐conjugated molecules. | ||
| 700 | 1 | |a He, Jing |4 aut | |
| 700 | 1 | |a Liu, Lin |4 aut | |
| 700 | 1 | |a Liu, Guoqin |4 aut | |
| 700 | 1 | |a Guo, Shengzhu |4 aut | |
| 700 | 1 | |a Lian, Zhe |4 aut | |
| 700 | 1 | |a Li, Xiaonan |4 aut | |
| 700 | 1 | |a Guo, Weijie |4 aut | |
| 700 | 1 | |a Chen, Xuebo |4 aut | |
| 700 | 1 | |a Wang, Ying |4 aut | |
| 700 | 1 | |a Jiang, Hua |4 aut | |
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