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Issue 42, 2016
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Fluorinated liquid crystals: evaluation of selectively fluorinated facially polarised cyclohexyl motifs for liquid crystal applications

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Abstract

This paper explores the synthesis of a series of prototype negative dielectric liquid crystalline (LC) compounds which contain fluorinated cyclohexane motifs. The series are analogues and differ only in that they contain between one to four fluorine atoms. The stereochemistry is such that all of the fluorines/C–F bonds are on one face of the cyclohexane ring. This follows from the recent recognition that cyclohexanes with fluorines orientated in one direction, perpendicular to the ring have a strong molecular dipole, a characteristic that might be an advantage in the design of negative dielectric materials. However it is found that the increased polarity, particularly with two or more oriented C–F bonds, leads to higher melting points and poorer solubility in test matrix formulations, relative to hydrocarbon liquid crystals. This arises due to electrostatic intermolecular interactions between the polarised cyclohexyl and aryl rings. The study highlights that in order to take advantage of these polar cyclohexane motifs for liquid crystal design, appropriate scaffolds are required which are free of aromatic rings and contain peripheral solubilising motifs.

Graphical abstract: Fluorinated liquid crystals: evaluation of selectively fluorinated facially polarised cyclohexyl motifs for liquid crystal applications

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Publication details

The article was received on 08 Sep 2016, accepted on 30 Sep 2016 and first published on 30 Sep 2016


Article type: Communication
DOI: 10.1039/C6OB01986B
Citation: Org. Biomol. Chem., 2016,14, 9974-9980
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    Fluorinated liquid crystals: evaluation of selectively fluorinated facially polarised cyclohexyl motifs for liquid crystal applications

    N. Al-Maharik, P. Kirsch, A. M. Z. Slawin, D. B. Cordes and D. O'Hagan, Org. Biomol. Chem., 2016, 14, 9974
    DOI: 10.1039/C6OB01986B

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