Pushing Steric Bias in the Scholl Reaction to Access Liquid Crystalline Crown Ethers

Sterically congested o-terphenyl crown ethers with alkoxy substituents at the 2,3,4-position or 3,4,5-position were synthesized from the corresponding tetrabromo­dibenzo­[15]­crown-5 and the corresponding boronic acids or borolanes via Suzuki cross-coupling and subsequently cyclized to the correspon...

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Bibliographic Details
Published in:Journal of organic chemistry 2014-11, Vol.79 (21), p.10143-10152
Main Authors: Wöhrle, Tobias, Kirres, Jochen, Kaller, Martin, Mansueto, Markus, Tussetschläger, Stefan, Laschat, Sabine
Format: Article
Language:English
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Summary:Sterically congested o-terphenyl crown ethers with alkoxy substituents at the 2,3,4-position or 3,4,5-position were synthesized from the corresponding tetrabromo­dibenzo­[15]­crown-5 and the corresponding boronic acids or borolanes via Suzuki cross-coupling and subsequently cyclized to the corresponding triphenylenes utilizing the Scholl reaction. Both series of compounds were investigated by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction (SAXS, WAXS) regarding their mesomorphic properties. While all but one of the 3,4,5-substituted derivatives displayed liquid crystalline behavior (Colh and Colr), only the 2,3,4-substititued triphenylene with the shortest alkoxy chains was liquid crystalline (Colr).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo501790d