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Issue 38, 2016
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Hydrogen bonding vs. molecule–surface interactions in 2D self-assembly of [C60]fullerenecarboxylic acids

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Abstract

The adsorption of C60-malonic derivatives C61(CO2H)2 and C66(CO2H)12 on Au(111) and a pentafluorobenzenethiol-modified Au substrate (PFBT@Au) has been investigated using scanning tunneling microscopy (STM) at a liquid–solid interface. Monofunctionalized C61(CO2H)2 forms a hexagonal close-packed overlayer on Au(111) and individual aligned dimers on PFBT@Au(111). The difference is attributed to the nature of the substrate⋯C61(CO2H)2 interaction (isotropic π–Au bonding vs. anisotropic PFBT⋯COOH interactions). Surprisingly, in both cases, the directionality of the COOH⋯COOH motif is compromised in favor of synergistic van der Waals/H bonding interactions. Such van der Waals contacts are geometrically unfeasible in hexafunctionalized C66(CO2H)12 and its assembly on Au(111) leads to a 2D molecular network controlled exclusively by H bonding. For both molecules, the “free” CO2H groups on the monolayer surface can engage in out-of-plane H bonding interaction resulting in the epitaxial growth of subsequent molecular layers.

Graphical abstract: Hydrogen bonding vs. molecule–surface interactions in 2D self-assembly of [C60]fullerenecarboxylic acids

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Supplementary files

Article information


Submitted
20 May 2016
Accepted
23 Aug 2016
First published
23 Aug 2016

Nanoscale, 2016,8, 16955-16962
Article type
Paper
Author version available

Hydrogen bonding vs. molecule–surface interactions in 2D self-assembly of [C60]fullerenecarboxylic acids

M. A. Mezour, R. M. Choueiri, O. Lukoyanova, R. B. Lennox and D. F. Perepichka, Nanoscale, 2016, 8, 16955
DOI: 10.1039/C6NR04115A

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