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

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Abstract

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 |β| (71.38 ± 3.4) and (84.25 ± 3.7) mkm−1 mol·pats−1 showed (E)-2-(4-chlorophenylmethylidene)-allobetuline and (2R,3R)-3-(4′-chlorophenyl)-2,2′-spiro-oxyranoallobetuline correspondingly. How the value of |β| 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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Acknowledgments

This work was performed using computational facilities of joint computational cluster of SSI “Institute for Single Crystals” and Institute for Scintillation Materials of National Academy of Science of Ukraine incorporated into Ukrainian National Grid.

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Authors and Affiliations

  1. State Scientific Institution “Institute for Single Crystals” of the National Academy of Sciences of Ukraine, Kharkiv, 61001, Ukraine

    Nikolay L. Babak, Oleg V. Shishkin, Svitlana V. Shishkina, Ivan M. Gella, Vladimir I. Musatov, Nataliya B. Novikova & Victoria V. Lipson

  2. Medicinal Chemistry Department, State Institution “V.Ya. Danilevsky Institute for Endocrine Pathology Problems” of the National Academy of Medical Sciences of Ukraine, Artema St., 10, Kharkiv, 61002, Ukraine

    Oleg V. Shishkin & Victoria V. Lipson

  3. V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv, 61122, Ukraine

    Svitlana V. Shishkina, Ivan M. Gella & Victoria V. Lipson

Authors
  1. Nikolay L. Babak
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  2. Oleg V. Shishkin
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  3. Svitlana V. Shishkina
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  4. Ivan M. Gella
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  5. Vladimir I. Musatov
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  6. Nataliya B. Novikova
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  7. Victoria V. Lipson
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Corresponding author

Correspondence to Svitlana V. Shishkina.

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Babak, N.L., Shishkin, O.V., Shishkina, S.V. et al. Synthesis and spatial structure of new chiral dopants from allobetuline series for cholesteric liquid-crystal compositions. Struct Chem 27, 295–303 (2016). https://doi.org/10.1007/s11224-015-0700-y

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  • DOI: https://doi.org/10.1007/s11224-015-0700-y

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