Two-dimensional self-assembly of a symmetry-reduced tricarboxylic acid

MacLeod, Jennifer M., Ben Chaouch, Zied, Perepichka, Dmitrii F., & Rosei, Federico (2013) Two-dimensional self-assembly of a symmetry-reduced tricarboxylic acid. Langmuir, 29(24), pp. 7318-7324.

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Abstract

Investigations of the self-assembly of simple molecules at the solution/solid interface can provide useful insight into the general principles governing supramolecular chemistry in two dimensions. Here, we report on the assembly of 3,4′,5-biphenyl tricarboxylic acid (H3BHTC), a small hydrogen bonding unit related to the much-studied 1,3,5-benzenetricarboxylic acid (trimesic acid, TMA), which we investigate using scanning tunneling microscopy (STM) and density functional theory (DFT) calculations. STM images show that H3BHTC assembles by itself into an offset zigzag chain structure that maximizes the surface molecular density in favor of maximizing the number density of strong cyclic hydrogen bonds between the carboxylic groups. The offset geometry creates “sticky” pores that promote solvent coadsorption. Adding coronene to the molecular solution produces a transformation to a high-symmetry host–guest lattice stabilized by a dimeric/trimeric hydrogen bonding motif similar to the TMA flower structure. Finally, we show that the H3BHTC lattice firmly immobilizes the guest coronene molecules, allowing for high-resolution imaging of the coronene structure.

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11 citations in Web of Science®

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ID Code: 89957
Item Type: Journal Article
Refereed: Yes
DOI: 10.1021/la3047593
ISSN: 1520-5827
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Copyright Owner: Copyright 2013 American Chemical Society
Deposited On: 04 Apr 2016 03:25
Last Modified: 15 Apr 2016 03:54

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