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Related Experiment Video

Updated: Mar 9, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

Published on: February 6, 2020

Versatile Dynamic Covalent Assemblies for Probing π-Stacking and Chirality Induction from Homotopic Faces.

Hebo Ye¹, Yu Hai^1,2, Yulong Ren¹

¹State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, 350002, P.R. China.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|January 3, 2017

Summary

This study introduces dynamic covalent reactions for π-stacking systems, enabling quantification of substituent effects. This method also facilitates chirality transfer, offering new avenues for studying weak interactions.

Keywords:

chirality dynamic covalent chemistry orthogonal assembly pi-interactions substituent effects

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Fabricating van der Waals Heterostructures with Precise Rotational Alignment

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Last Updated: Mar 9, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly

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Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

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Fabricating van der Waals Heterostructures with Precise Rotational Alignment

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Published on: July 5, 2019

Area of Science:

Supramolecular Chemistry
Organic Chemistry

Background:

Quantifying substituent effects in π-stacking interactions remains challenging.
Dynamic covalent chemistry offers a versatile platform for molecular assembly.

Purpose of the Study:

To develop a novel method for building and quantifying π-stacking model systems using dynamic covalent reactions (DCRs).
To investigate the substituent effects (SEs) in π-stacking interactions.
To explore the potential for chirality transfer within these DCR-assembled systems.

Main Methods:

Discovery of a general DCR between 10-methylacridinium ion and primary amines.
In situ quantification of SEs using competing π-stacking systems via amine exchange.
Analysis of substituent effects using Hammett plots.
Chirality transfer studies using α-chiral amines.

Main Results:

A general DCR was established, where π-stacking stabilizes the adduct.
SEs were quantified and shown to be dominated by electrostatic contributions, correlating linearly with σm.
The additivity of SEs supports a direct interaction model.
Chirality transfer from α-chiral amines to homotopic faces was achieved via π-stacking.

Conclusions:

Dynamic covalent assembly provides a powerful strategy for probing weak interactions like π-stacking.
This approach allows for facile quantification of SEs and demonstrates control over chirality transfer.
The methodology holds promise for future research in supramolecular chemistry and chiral manipulation.