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Updated: Dec 16, 2025

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

π covalency in the halogen bond.

Cameron W Kellett¹, Pierre Kennepohl¹, Curtis P Berlinguette^2,3,4,5

¹Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, BC, V6T 1Z1, Canada.

Nature Communications

|July 5, 2020

Summary

This study reveals π-covalency in halogen bonds, challenging the hydrogen bond analogy. Halogen bonds are better understood as metal coordination bonds, offering new ways to tune molecular electronics.

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Area of Science:

Chemistry
Chemical Biology
Materials Science

Background:

Halogen bonds are directional intermolecular interactions crucial in chemistry and chemical biology.
Current models liken halogen bonds to hydrogen bonds, focusing on their σ-symmetric component.
The potential for π-covalency in halogen bonds remains unexplored in existing theoretical frameworks.

Purpose of the Study:

To investigate the presence and implications of π-covalency in halogen bonds.
To re-evaluate the established analogy between halogen bonds and hydrogen bonds.
To propose a revised model for understanding halogen bonding.

Main Methods:

Computational analysis of chlorine K-edge X-ray absorption spectra.
Study of halogen bonds formed between chloride and halogenated triphenylamine-based radical cations.

Main Results:

Evidence of π-covalency was found in the studied halogen bonds.
The findings indicate that π-covalency is an operative component of these interactions.
Computational analysis supported the experimental observations.

Conclusions:

Halogen bonding exhibits π-covalency, a feature not accounted for in hydrogen bond models.
Halogen bonds are more accurately described by analogy to metal coordination bonds.
This revised understanding opens new avenues for utilizing halogen bonds to modulate electronic properties of conjugated systems.