Stereoisomerism in Trimacrocyclic Structures Fused by a Pillar[6]arene and Two [8]Cycloparaphenylenes

Stereoisomerism in pillararenes, particularly chiral isomerism from atropisomers, has intrigued organic chemists. Herein, we report the synthesis and characterization of a trimacrocyclic system formed by fusing two [8]cycloparaphenylenes with a pillar[6]arene. This system exhibits unique stereoisomerism, yielding a racemic mixture and a <i>meso</i> compound. The isomers were characterized using NMR, HRMS, and single crystal X-ray diffraction. This study offers valuable insights into constructing chiral isomers in macrocycles and enriches our understanding of stereochemistry.

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Publication Details

Journal
Organic Letters
Published
2025-04-13
DOI
https://doi.org/10.1021/acs.orglett.5c01097
Citations
7
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
Field-Weighted Citation Impact
6.55

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article

Stereoisomerism in Trimacrocyclic Structures Fused by a Pillar[6]arene and Two [8]Cycloparaphenylenes

Chuyang Cheng, Jiao Ming, Dongmei Zhang, Hanchi Zhong et al.
7 citations
Organic Letters
Synthesis and Properties of Aromatic Compounds
6.55
article

Stereoisomerism in Trimacrocyclic Structures Fused by a Pillar[6]arene and Two [8]Cycloparaphenylenes

Chuyang Cheng, Jiao Ming, Dongmei Zhang, Hanchi Zhong, Kai Lan
article en
7 citations

Abstract

Stereoisomerism in pillararenes, particularly chiral isomerism from atropisomers, has intrigued organic chemists. Herein, we report the synthesis and characterization of a trimacrocyclic system formed by fusing two [8]cycloparaphenylenes with a pillar[6]arene. This system exhibits unique stereoisomerism, yielding a racemic mixture and a <i>meso</i> compound. The isomers were characterized using NMR, HRMS, and single crystal X-ray diffraction. This study offers valuable insights into constructing chiral isomers in macrocycles and enriches our understanding of stereochemistry.

Organic LettersVol. 27(16)
Sichuan University (CN)
National Natural Science Foundation of China, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 3%
Synthesis and Properties of Aromatic Compounds
6.55
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