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Toward Two-Dimensional Tessellation through Halogen Bonding between Molecules and On-Surface-Synthesized Covalent

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¹CEA, CNRS, SPEC, TITANS, Université Paris-Saclay, F-91191 Gif sur Yvette, France.

International Journal of Molecular Sciences

|July 29, 2023

Summary

Researchers explored creating 2D organic nanoarchitectures using triangular molecules and covalent multimers. They found that achieving a perfect semi-regular tiling requires specific building blocks that do not coexist at the necessary temperatures.

Keywords:

covalent Ullmann coupling molecule on-surface synthesis self-assembly tessalion tilings

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Area of Science:

Materials Science
Surface Chemistry
Nanotechnology

Background:

Engineering complex two-dimensional (2D) organic nanoarchitectures is crucial for advanced materials.
On-surface synthesis offers a pathway to create intricate molecular structures.
Controlling self-assembly of bespoke molecular building blocks is key to designing functional nanomaterials.

Purpose of the Study:

To investigate the engineering of 2D tessellation organic nanoarchitectures using triangular molecules.
To explore the formation of covalent multimers via on-surface synthesis.
To understand the self-assembly behavior and limitations in achieving specific tiling patterns.

Main Methods:

Scanning tunneling microscopy (STM) was employed to visualize the nanoarchitectures.
Ullmann coupling was induced by depositing 1,3,5-Tris(3,5-dibromophenyl)benzene molecules on Au(111) surfaces at controlled temperatures.
Analysis of molecular self-assembly and superstructure formation was performed.

Main Results:

A semi-regular rhombitrihexagonal tiling superstructure was observed at 145 °C, composed of intact triangular molecules and covalent dimers.
The structure featured triangular domains of intact molecules and rectangular rows of covalent dimers.
Nearly hexagonal vertices were formed by covalent multimers.
A perfect semi-regular tiling was not achieved due to the absence of coexisting covalent hexagons.

Conclusions:

The formation of specific 2D organic tessellation nanoarchitectures depends critically on the synthesis and ratio of molecular building blocks.
The required covalent hexagons for a perfect rhombitrihexagonal tiling only form above 165 °C and do not coexist with the necessary dimers and intact molecules at lower temperatures.
Precise control over temperature is essential for directing on-surface synthesis and achieving desired self-assembled structures.