Lemniscular carbon nanohoops with contiguous conjugation from planar chiral [2.2]paracyclophane: influence of the regioselective synthesis on topological chirality

He, Jing; Yu, Mohan; Lian, Zhe; Fan, Yan–Qing; Guo, Shengzhu; Li, Xiaonan; Wang, Ying; Wang, Wenguang; Cheng, Zhi-Yun; Jiang, Hua

doi:10.1039/d2sc06825g

Cited by 30 publications

(7 citation statements)

References 77 publications

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“…in bismacrocycles, compounds with the capability to bind to multiple, distinct guests can be obtained. 261–266 For example, Cong and coworkers reported a conjugated figure-of-eight oligoparaphenylene nanohoop ( 40 ) with adaptive cavities that can form 1 : 2 host–guest complexes with C 60 and C 70 . 267 More recently, Xu, Yam and von Delius reported the synthesis of two [ n ]cycloparaphenylene-pillar[5]arene ([ n ]CPP-P[5]A, n = 8 and 10) bismacrocycles by integrating P[5]A into the [ n ]CPP backbone.…”

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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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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“…HPP 2 is a chiral luminophore with a moderate luminescence dissymmetry factor of 2.2×10 -3 . The measured brightness of CPL, BCPL = 63, is relatively high compared to other chiral carbon nanohoops [36][37][38][39][40][41] and superior to known [6]helicene derivatives. [42][43][44] The configurational stability endowed to the enantiomers of 2 by the presence of [6]helicene in the structure did not allow us to experimentally observe a racemization of the enantiopure samples even upon heating.…”

mentioning

confidence: 83%

Topological Bistability of the π-System in a Helicene Carbon Nanohoop

Šolomek,

Malinčík

2023

Synlett

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Molecules with a π-system that can be mapped onto a Möbius band may display Möbius aromaticity. Such molecules are difficult to synthesize because they have a twisted structure. Recently, we combined chiral [6]helicene and fluorescent [7]cycloparaphenylene and synthesized the first helicene para-phenylene ([6,7]HPP) carbon nanohoop. We have demonstrated that this design strategy ultimately provides Möbius topology of the molecular π-electron system and, therefore, offers the potential to study Möbius aromaticity experimentally. In addition, the synthesized nanohoop exists as a mixture of conformers in a solution. Some of the conformers possess a different orientability of their π-systems, i.e., they differ in their topology. As a result, the recorded circularly polarized luminescence of isolated enantiomers displays both the left and right handedness of the emitted light, each emanating from a conformer with different π-system topology. Therefore, [6,7]HPP provided the first experimental evidence of such topological bistability in carbon nanohoops.

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“…49 Carbon nanorings are commonly subjected to geometry optimization using the B3LYP functional, which demonstrates remarkable efficacy in predicting both structural parameters and harmonic frequencies. 35,40,50,51 This study involves geometry optimizations of [8]CPP-[10]cyclacene under the external electric fields and employs the broken-symmetry spin-unrestricted method at the UB3LYP/6-31G(d) level. When a small external electric field is applied, the results indicate that the total energy value obtained using the UB3LYP method is slightly lower than that achieved by the B3LYP method.…”

Section: Methodsmentioning

confidence: 99%