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http://dx.doi.org/10.18419/opus-14299
Autor(en): | Bühlmeyer, Andrea Ehni, Philipp Ullmann, Dustin Frey, Wolfgang Baro, Angelika Laschat, Sabine |
Titel: | Synthesis and liquid crystalline self‐assembly of concave diindoles with a hydropentalene core |
Erscheinungsdatum: | 2021 |
Dokumentart: | Zeitschriftenartikel |
Seiten: | 1452-1465 |
Erschienen in: | European journal of organic chemistry 2021 (2021), S. 1452-1465 |
URI: | http://nbn-resolving.de/urn:nbn:de:bsz:93-opus-ds-143184 http://elib.uni-stuttgart.de/handle/11682/14318 http://dx.doi.org/10.18419/opus-14299 |
ISSN: | 1099-0690 1434-193X |
Zusammenfassung: | Fischer indole reaction of Weiss diketone with 4‐bromophenylhydrazine provided the 2,8‐dibromo‐hexahydropentaleno[2,1‐b:5,4‐b’]diindole key intermediate, which was converted to the target compounds by N‐protection/Suzuki cross‐coupling. Variation of protecting groups, mesogenic units, and their alkoxy substitution gave calamitic diindole mesogens. Both N‐protection and alkoxy chain influenced the mesomorphic properties of phenyl diindoles. Among the differently N‐protected derivatives only ethylcarbamate‐protected ones formed enantiotropic mesophases. Mesophase range and type were controlled by the chain lengths: chains≤C12 gave nematic (N) phases, diindoles with side chains≥C14 formed additional lower temperature smectic (SmA) phases. Irrespective of the chain lengths 4′‐alkyloxybiphenyl diindoles formed N and SmA phases upon first heating but tended to decomposition below their clearing points. X‐ray crystal structure analysis of bis(4′‐decyloxy)biphenyl diindole reveals that in the solid‐state the folding angle of the hydropentalene core caused an almost perpendicular orientation of the two indole/biphenyl parts with respect to each other. |
Enthalten in den Sammlungen: | 03 Fakultät Chemie |
Dateien zu dieser Ressource:
Datei | Beschreibung | Größe | Format | |
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EJOC_EJOC202001656.pdf | 3,78 MB | Adobe PDF | Öffnen/Anzeigen |
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