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From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
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Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly
Bao Zha1, Meiqiu Dong1, Xinrui Miao1
1College of Materials Science and Engineering, South China University of Technology , Guangzhou 510640, China.
The Journal of Physical Chemistry Letters
|August 3, 2016
Summary
Researchers explored how ester group orientation in thienophenanthrene derivatives influences halogen bonding. This control over intermolecular interactions dictates the formation of distinct 2D molecular self-assembled patterns on surfaces.
Area of Science:
- Supramolecular Chemistry
- Surface Science
- Organic Chemistry
Background:
- Halogen bonding is a crucial noncovalent interaction for designing 2D molecular architectures on surfaces due to its specificity and directionality.
- Controlling molecular self-assembly requires a deep understanding of the factors influencing halogen bond formation and strength.
Purpose of the Study:
- To investigate how the orientation of ester substituents in thienophenanthrene derivatives impacts halogen bonding.
- To elucidate the relationship between halogen bonding, charge distribution, and the resulting self-assembled patterns on surfaces.
- To explore the role of various weak interactions, including halogen bonds and hydrogen bonds, in directing molecular arrangement.
Main Methods:
- Density Functional Theory (DFT) calculations to analyze the positive charge distribution on halogen atoms.
- Scanning Tunneling Microscopy (STM) to visualize and characterize the self-assembled molecular patterns on surfaces.
- Systematic variation of halogen substituents to study their effect on molecular arrangement.
Main Results:
- Ester substituent orientation significantly affects halogen charge distribution, thereby controlling intermolecular halogen bond formation.
- Different self-assembled patterns were observed, driven by a combination of heterohalogen bonds (X···O═C, X···S), hydrogen bonds (H···Br, H···O), and I···I interactions.
- The strength and directionality of these weak interactions were found to be key determinants of the observed molecular arrangements.
Conclusions:
- This study provides critical insights into how ester orientation influences halogen bonding and subsequent self-assembly.
- Understanding the interplay of various weak interactions is essential for designing and controlling 2D molecular architectures.
- The findings are relevant for identifying and utilizing multiple halogen bonding strategies in supramolecular chemistry.
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