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Related Experiment Video

Updated: Jun 9, 2025

Construction and Systematical Symmetric Studies of a Series of Supramolecular Clusters with Binary or Ternary Ammonium Triphenylacetates

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Published on: February 15, 2016

Interwoven Trimeric Cage-Catenanes with Topological Chirality.

Lihua Chen¹, Zhenghong Chen¹, Weihao Wang¹

¹School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China.

Journal of the American Chemical Society

|October 22, 2024

Summary

Researchers synthesized an interwoven trimeric cage-catenane using dynamic imine chemistry. This novel structure exhibits topological chirality and is thermodynamically favored over linear isomers, offering new avenues for complex molecular architectures.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Area of Science:

Supramolecular Chemistry
Organic Synthesis
Materials Science

Background:

Catenanes, molecules interlocked like links in a chain, are known for topological chirality.
Previous research primarily focused on catenanes made of single rings, with multiring systems being rare due to synthetic challenges.
Efficient strategies for synthesizing complex, multiannulated catenanes are limited.

Purpose of the Study:

To develop a one-pot synthesis for interwoven catenanes of multiannulated monomers.
To investigate the driving forces and thermodynamic favorability of the cage-catenane formation.
To explore the topological chirality of the synthesized structure.

Main Methods:

One-pot dynamic imine condensation reaction between diamine linkers and trialdehyde panels.
Topology-based statistical modeling to predict isomer formation probabilities.
Chiral-high-performance liquid chromatography (HPLC), circular dichroism (CD) spectroscopy, and single-crystal X-ray diffraction (XRD) for structural and chiral analysis.

Main Results:

Successful high-yield synthesis of a trimeric cage-catenane driven by 6-fold π-π stacking.
The interwoven cage-catenane is thermodynamically more stable than its monomeric precursor and linear isomers.
The interwoven structure is the dominant species, with formation probability significantly enhanced by π-π stacking effects.
Topological chirality was confirmed, with XRD revealing a pair of enantiomers despite achiral monomers.

Conclusions:

A facile one-pot method for synthesizing interwoven trimeric cage-catenanes has been established.
The study demonstrates the significant role of π-π stacking in directing the formation of complex interwoven architectures.
The findings provide a rational design strategy for creating topologically intricate and chiral molecular structures.