Chiral Carbon Nanorings: Synthesis, Properties and Hierarchical Self‐assembly of Chiral Ternary Complexes Featuring a Narcissistic Chiral Self‐Recognition for Chiral Amines

Fan, Yan–Qing; He, Jing; Liu, Lin; Liu, Guoqin; Guo, Shengzhu; Lian, Zhe; Li, Xiaonan; Guo, Weijie; Chen, Xuebo; Wang, Ying; Jiang, Hua

doi:10.1002/anie.202304623

Cited by 31 publications

(14 citation statements)

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“…[181][182][183][184][185][186][187][188][189][190] Additionally, fully conjugated This journal is © The Royal Society of Chemistry 2024 macrocycles like [n]CPPs, cyclo-porphyrins, and [n]cyclo-2,8chrysenylenes with well-defined diameters and unique radial conjugation exhibit fascinating electronic and optical properties. [191][192][193][194][195][196][197][198][199][200][201][202][203][204] These shape-persistent macrocycles offer significant advantages in constructing 1D nanotubes, 2D networks, and 3D complexes via self-assembly. 205 This review article primarily focusses on covalent macrocycles and metallomacrocycles, which have demonstrated their effectiveness as hosts for fullerene recognition (Fig.…”

Section: Macrocycles As Fullerene Hostsmentioning

confidence: 99%

“…181–190 Additionally, fully conjugated macrocycles like [ n ]CPPs, cyclo-porphyrins, and [ n ]cyclo-2,8-chrysenylenes with well-defined diameters and unique radial conjugation exhibit fascinating electronic and optical properties. 191–204 These shape-persistent macrocycles offer significant advantages in constructing 1D nanotubes, 2D networks, and 3D complexes via self-assembly. 205…”

Section: Fullerene Host–guest Chemistrymentioning

confidence: 99%

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Recent advances in supramolecular fullerene chemistry

Chang,

Xu,

von Delius

2024

Chem. Soc. Rev.

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Section: Macrocycles As Fullerene Hostsmentioning

confidence: 99%

Section: Fullerene Host–guest Chemistrymentioning

confidence: 99%

Recent advances in supramolecular fullerene chemistry

Chang,

Xu,

von Delius

2024

Chem. Soc. Rev.

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“…This behavior is indicative of the typical FRET process, which suggests that energy transfer occurs from TP- [12]CPP to G1 due to the formation of the Russian doll complexes. The apparent binding constant 11,39 of TP- [12]CPP for G1⊂P5A was estimated to be 3.5 × 10 4 M −1 (Table 1 and Figure S22), which is obviously higher than that of TP- [12]CPP for P5A, thereby indicating that the presence of G1 enhances the binding affinity between TP- [12]CPP and P5A. This finding is consistent with that of the Russian dolls reported by Stoddart et al 11 The efficiency of energy transfer (Φ ET ) was calculated to be 78% according to the previous reports (Table 1 and the Supporting Information).…”

Section: Construction Of Ring-in-ring Complex Of P5a⊂tp-[12]cppmentioning

confidence: 99%

Monitoring Hierarchical Assembly of Ring-in-Ring and Russian Doll Complexes Based on Carbon Nanoring by Förster Resonance Energy Transfer

Guo,

Liu,

et al. 2024

JACS Au

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We presented the construction of the ring-in-ring and Russian doll complexes on the basis of triptycene-derived carbon nanoring (TP-[12]CPP), which not only acts as a host for pillar[5]arene (P5A) but also serves as an energy donor for building Forster resonance energy transfer (FRET) systems. We also demonstrated that their hierarchical assembly processes could be efficiently monitored in real time using FRET. NMR, UV−vis and fluorescence, and mass spectroscopy analyses confirmed the successful encapsulation of the guests P5A/P5A-An by TP-[12]CPP, facilitated by C−H•••π and •••π interactions, resulting in the formation of a distinct ring-in-ring complex with a binding constant of K a = 2.23 × 10 4 M −1 . The encapsulated P5A/P5A-An can further reverse its role to be a host for binding energy acceptors to form Russian doll complexes, as evidenced by the occurrence of FRET and mass spectroscopy analyses. The apparent binding constant of the Russian doll complexes was up to 3.6 × 10 4 M −1 , thereby suggesting an enhanced synergistic effect. Importantly, the Russian doll complexes exhibited both intriguing one-step and sequential FRET dependent on the subcomponent P5A/P5A-An during hierarchical assembly, reminiscent of the structure and energy transfer of the light-harvesting system presented in purple bacteria.

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“…Chiral framework materials are rapidly developing as a novel form of chiral material, and play an essential role in the fields of chiral recognition, 60 sensing, 61 chiral separation, 62 asymmetric catalysis, 63 drug delivery 64 and chiral emission materials. 65 Cao and coworkers 66 succeeded in constructing a dynamic chiral SOF based on TPE 's P / M rotational conformation in order to explore chiral recognition using the constrained structure and dynamic assembly properties of SOF material.…”

Section: Two- Dimensional (2d) Supramolecular Organic Luminescent Ass...mentioning

confidence: 99%