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Issue 5, 2017
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Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents

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Abstract

Novel [15]crown-5 and [18]crown-6 o-terphenyls differing in number and position of sulfur in the side chains and their corresponding triphenylene analogues were synthesized via a nucleophilic aromatic displacement of fluoride as the key step. Except for one short chain derivative all other compounds showed enantiotropic columnar mesophases which were studied by DSC, POM and XRD (WAXS, SAXS). The presence of sulfur induced broad room temperature columnar mesophases. This effect was more pronounced for bend [15]crown-5 derivatives than for linear [18]crown-6 derivatives. Redox properties were mostly governed by the triphenylene moieties, showing stepwise oxidation of the individual triphenylene units.

Graphical abstract: Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents

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Publication details

The article was received on 26 Jan 2017, accepted on 06 Mar 2017 and first published on 07 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00077D
Citation: Org. Chem. Front., 2017,4, 790-803
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    Tuning liquid crystalline phase behaviour in columnar crown ethers by sulfur substituents

    J. Kirres, K. Schmitt, I. Wurzbach, F. Giesselmann, S. Ludwigs, M. Ringenberg, A. Ruff, A. Baro and S. Laschat, Org. Chem. Front., 2017, 4, 790
    DOI: 10.1039/C7QO00077D

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