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Volume 204, 2017
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Molecular self-assembly of substituted terephthalic acids at the liquid/solid interface: investigating the effect of solvent

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Abstract

Self-assembly of three related molecules – terephthalic acid and its hydroxylated analogues – at liquid/solid interfaces (graphite/heptanoic acid and graphite/1-phenyloctane) has been studied using a combination of scanning tunnelling microscopy and molecular mechanics and molecular dynamics calculations. Brickwork-like patterns typical for terephthalic acid self-assembly have been observed for all three molecules. However, several differences became apparent: (i) formation or lack of adsorbed monolayers (self-assembled monolayers formed in all systems, with one notable exception of terephthalic acid at the graphite/1-phenyloctane interface where no adsorption was observed), (ii) the size of adsorbate islands (large islands at the interface with heptanoic acid and smaller ones at the interface with 1-phenyloctane), and (iii) polymorphism of the hydroxylated terephthalic acids’ monolayers, dependent on the molecular structure and/or solvent. To rationalise this behaviour, molecular mechanics and molecular dynamics calculations have been performed, to analyse the three key aspects of the energetics of self-assembly: intermolecular, substrate–adsorbate and solvent–solute interactions. These energetic characteristics of self-assembly were brought together in a Born–Haber cycle, to obtain the overall energy effects of formation of self-assembled monolayers at these liquid/solid interfaces.

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Publication details

The article was received on 20 Mar 2017, accepted on 12 Apr 2017 and first published on 12 Apr 2017


Article type: Paper
DOI: 10.1039/C7FD00112F
Citation: Faraday Discuss., 2017,204, 191-213
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    Molecular self-assembly of substituted terephthalic acids at the liquid/solid interface: investigating the effect of solvent

    A. Della Pia, D. Luo, R. Blackwell, G. Costantini and N. Martsinovich, Faraday Discuss., 2017, 204, 191
    DOI: 10.1039/C7FD00112F

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