A convenient one-pot synthesis, and characterisation of the ω-bromo-1-(4-cyanobiphenyl-4’-yl) alkanes (CBnBr)

Calum Jordan Gibb, John M. D. Storey, Corrie T. Imrie* (Corresponding Author)

*Corresponding author for this work

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11 Citations (Scopus)
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A convenient synthetic route based on a sodium-mediated aromatic cross-coupling reaction is described for the multi-gram preparation of the ω-bromo-1-(4-cyanobiphenyl-4’−yl) alkanes (CBnBr, n = 2–10). These materials are not only key intermediates in the synthesis of oligomers and polymers but also exhibit fascinating liquid crystal behaviour in their own right. Nematic behaviour is observed for n⩾5, and the nematic-isotropic transition temperature, TNI, increases in essentially a linear manner on n. The properties of the ω-bromo-1-(4-cyanobiphenyl-4’−yloxy) alkanes (CBOnBr, n = 2–9) are also reported, and nematic behaviour is seen for n⩾3. The values of TNI show a weak odd-even effect on n in which the odd members show the higher values. The sense of this alternation is opposite to that seen for the 4-alkyloxy-4’-cyanobiphenyls, and this is attributed to the steric bulk of the bromine atom. The absence of smectic behaviour for both the CBnBr and CBOnBr series is attributed largely to electrostatic interactions that would arise from the concentration of the bromine atoms at the layer interfaces in an interdigitated smectic phase. A comparison of a range of cyanobiphenyl-based materials containing a chain with a terminal polar or polarisable group suggests that their phase behaviour is governed largely by their average molecular shapes.

Original languageEnglish
Pages (from-to)1706-1716
Number of pages12
JournalLiquid Crystals
Issue number12
Early online date28 Jun 2022
Publication statusPublished - 28 Jun 2022

Bibliographical note

Open access via T&F agreement


  • Cross-Coupling
  • reductive alkylation
  • cyanobipheny
  • halogen terminated
  • smectic phase suppresion


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