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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Published inJournal of organic chemistry Vol. 79; no. 21; pp. 10143 - 10152
Main Authors Wöhrle, Tobias, Kirres, Jochen, Kaller, Martin, Mansueto, Markus, Tussetschläger, Stefan, Laschat, Sabine
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.11.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DYES
MECHANISM
NEUTRAL CARRIERS
ARENES
COLUMNAR MESOPHASES
MEMBRANES
CHAINS
SELF-ORGANIZATION
EFFICIENT
UNITS
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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).
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo501790d