Binaphthyl-derived armchair-type molecular carbon rings with chirality: synthesis and optical properties

Huang, Qiang; Zhang, Jinling; Chen, Huafeng; Kong, Xin; Xu, Peng; Du, Pingwu

doi:10.1039/d2qo01977a

Cited by 5 publications

(4 citation statements)

References 41 publications

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“…Unlike the previously reported chiral carbon nanotubes (CNTs), which derive their chirality from the lack of a plane of symmetry or a molecular inversion center, Du and Xu [ 25 ] have recently synthesized two armchair carbon ring CNTs ( R ‐ 39 and S ‐ 39 ) ( Figure ). Geometry optimization and NMR spectrums revealed that the two OEt groups were located in the inner and outer sides of nanorings.…”

Section: π‐Conjugated Chiral Macrocycles In Circularly Polarized Lumi...mentioning

confidence: 99%

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Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

Xue,

Shi,

Chen

2024

Advanced Optical Materials

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Molecular chirality plays a pivotal role across the disciplines of chemical and physical sciences, as well as holding significant implications in the realms of medicine and technology. Chiral macrocycles have attracted recent interests in synthetic chemistry, material science, and supramolecular chemistry. Due to the cyclic arrangements of stereogenic elements or special orientations confined in the rigid structures, π‐conjugated chiral macrocycles are expected to be highly luminescent, and configurationally stable, and thus serve to develop high‐performance chiroptical materials. Given the rapid progress achieved in this new area in recent years, it is significant to highlight new concepts and breakthroughs. This minireview will offer the overview of a wide range of π‐conjugated chiral macrocycles from traditional molecules which include the axially, helically, and planar chiral skeletons to the new chiral nanobelts with a focus on the structure‐function relationship between chiral molecules and the unique chiroptical properties.

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Section: π‐Conjugated Chiral Macrocycles In Circularly Polarized Lumi...mentioning

confidence: 99%

Section: π‐Conjugated Chiral Macrocycles In Circularly Polarized Lumi...mentioning

confidence: 99%

Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

Xue,

Shi,

Chen

2024

Advanced Optical Materials

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“…Nanorings 6 n displays size‐dependent photophysical properties and is synthesized directly through platinum‐mediated assembly of BINOL derivative 5 units. Our ongoing efforts aim to introduce chirality into armchair‐type CNT segments by incorporating BINOL chiral units, thereby broadening the scope of CNT segments with chiral attributes [31] . The enantiomers ( R )/( S )‐ 7 were successfully synthesized and characterized through circular dichroism (CD) spectral analysis.…”

Section: Binol‐based Chiral Macrocyclesmentioning

confidence: 99%

“…Our ongoing efforts aim to introduce chirality into armchair-type CNT segments by incorporating BINOL chiral units, thereby broadening the scope of CNT segments with chiral attributes. [31] The enantiomers (R)/(S)-7 were successfully synthesized and characterized through circular dichroism (CD) spectral analysis. Additionally, the Φ PL of compound 7 was determined to be 54 % (Figure 3b).…”

Section: Binol-based Chiral Macrocyclesmentioning

confidence: 99%

BINOL‐Based Chiral Macrocycles and Cages

Yu,

Hu,

Ning

et al. 2024

Angewandte Chemie

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Chirality, a fundamental principle in chemistry, biology, and medicine, is prevalent in nature and in organisms. Chiral molecules, such as DNA, RNA, and proteins, are crucial in biomolecular synthesis, as well as in the development of functional materials. Among these, 1,1´‐binaphthyl‐2,2´‐diol (BINOL) stands out for its stable chiral configuration, versatile functionality, and commercial availability. BINOL is widely employed in asymmetric catalysis and chiral materials. This review mainly focuses on recent research over the past five years concerning the use of BINOL derivatives for constructing chiral macrocycles and cages. Their contributions to chiral luminescence, enantiomeric separation, transmembrane transport, and asymmetric catalysis were examined.

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Polycationic Open‐Shell Cyclophanes: Synthesis of Electron‐Rich Chiral Macrocycles, and Redox‐Dependent Electronic States

Shi,

Li,

et al. 2024

Angewandte Chemie

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π‐Conjugated chiral nanorings with intriguing electronic structures and chiroptical properties have attracted considerable interests in synthetic chemistry and materials science. We present the design principles to access new chiral macrocycles (1 and 2) that are essentially built on the key components of main‐group electron‐donating carbazolyl moieties or the π‐expanded aza[7]helicenes. Both macrocycles show the unique molecular conformations with a (quasi) figure‐of‐eight topology as a result of the conjugation patterns of 2,2’,7,7’‐spirobifluorenyl in 1 and triarylamine‐coupled aza[7]helicene‐based building blocks in 2. This electronic nature of redox‐active, carbazole‐rich backbones enabled these macrocycles to be readily oxidized chemically and electrochemically, leading to the sequential production of a series of positively charged polycationic open‐shell cyclophanes. Their redox‐dependent electronic states of the resulting multispin polyradicals have been characterized by VT‐ESR, UV−vis−NIR absorption and spectroelectrochemical measurements. The singlet (ΔES‐T = ‒1.29 kcal mol‒1) and a nearly degenerate singlet‐triplet ground state (ΔES‐T(calcd) = ‒0.15 kcal mol‒1 and ΔES‐T(exp) = 0.01 kcal mol‒1) were proved for diradical dications 12+2• and 22+2•, respectively. Our work provides an experimental proof for the construction of electron‐donating new chiral nanorings, and more importantly for highly charged polyradicals with potential applications in chirospintronics and organic conductors.

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Binaphthyl-derived armchair-type molecular carbon rings with chirality: synthesis and optical properties

Abstract: Herein, we report the synthesis of binaphthyl-derived hoop-shaped aromatic hydrocarbon enantiomers (RCR, SCR) as segments of (9,9) armchair CNTs. After the structures were identified by HR-MS and NMR, further circular...

Cited by 5 publications

References 41 publications

Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

Circularly Polarized Luminescent π‐Conjugated Chiral Nanorings and Nanobelts

BINOL‐Based Chiral Macrocycles and Cages

Polycationic Open‐Shell Cyclophanes: Synthesis of Electron‐Rich Chiral Macrocycles, and Redox‐Dependent Electronic States

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