4.3 Article

Synthesis and spatial structure of new chiral dopants from allobetuline series for cholesteric liquid-crystal compositions

Journal

STRUCTURAL CHEMISTRY
Volume 27, Issue 1, Pages 295-303

Publisher

SPRINGER/PLENUM PUBLISHERS
DOI: 10.1007/s11224-015-0700-y

Keywords

Allobetuline derivatives; Chiral dopants for cholesteric liquid-crystal compositions; Helical twisting power; Molecular structure; Quantum-chemical calculations

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New series of chiral dopants for cholesteric liquid-crystal compositions were synthesized on the base of 2-substituted allobetuline derivatives, and their steric structure was determined by X-ray analysis. The relationship between spatial structure of these compounds and their ability to induce cholesteric helix in 4-pentyl-4'-cyanobiphenyl nematic solvent was examined. The highest values of the helical twisting power |beta| (71.38 +/- A 3.4) and (84.25 +/- A 3.7) mkm(-1) mol center dot pats(-1) showed (E)-2-(4-chlorophenylmethylidene)-allobetuline and (2R,3R)-3-(4'-chlorophenyl)-2,2'-spiro-oxyranoallobetuline correspondingly. How the value of |beta| in this series of compounds varies depending on the spatial arrangement relative to the aryl moiety of the chiral core is shown.

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