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Issue 5, 2009
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Crown ethers with lateral ortho-terphenyl units: effect of ester groups and sodium salts on the mesomorphic properties

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Abstract

Unsymmetrical crown ether derivatives 7 and 12 with one lateral o-terphenyl unit bearing different ester substituents were synthesized starting from methoxymethyl (MOM) protected bromobenzenes 3 and 8 by conversion into the respective borolanes 4 and 9, twofold Suzuki coupling with dibromobenzo[15]crown-5, acidic deprotection and finally esterification either with various alkanoic chlorides or gallic acids. Reaction with NaI provided the complexes [NaI·(7a–g)] and [NaI·(12a–d)], respectively. Uncomplexed crown ethers as well as their complexes [NaI·7a–c] and [NaI·12a–d] are non-mesogenic. In the case of [NaI·(7d–g)], however, the complexation induced a mesophase formation. As exemplarily shown for [NaI·7d], different textures were observed upon cooling, a fan-shaped texture, which is typical for a columnar hexagonal mesophase, and a striped fan-shaped texture, indicating a second mesophase Colx at low-temperature. From the SAXS diffraction pattern this mesophase was assigned to be columnar rectangular. For [NaI·7g] a different diffraction pattern was found, from which the low-temperature mesophase might be attributed to a soft crystal or a highly ordered columnar mesophase with orthorhombic symmetry.

Graphical abstract: Crown ethers with lateral ortho-terphenyl units: effect of ester groups and sodium salts on the mesomorphic properties

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Publication details

The article was received on 21 Aug 2008, accepted on 12 Nov 2008 and first published on 16 Dec 2008


Article type: Paper
DOI: 10.1039/B814536A
J. Mater. Chem., 2009,19, 645-654

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    Crown ethers with lateral ortho-terphenyl units: effect of ester groups and sodium salts on the mesomorphic properties

    N. Steinke, M. Jahr, M. Lehmann, A. Baro, W. Frey, S. Tussetschläger, S. Sauer and S. Laschat, J. Mater. Chem., 2009, 19, 645
    DOI: 10.1039/B814536A

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