The synthesis and characterization of two benzyloxy-terminated
isoxazole liquid crystals, (ILCs) 7a (n-octyl) and 7b (n-decyl), are described.
The synthesis of the five-membered isoxazole ring was based on the
(3 + 2) 1,3-dipolar cycloaddition to furnish the isoxazoline cycloadduct
and the subsequent MnO2-oxidation. The liquid crystal (LC)
behavior was accomplished by polarized optical microscopy (POM), differential
scanning calorimetry, single-crystal X-ray diffraction, X-ray diffraction
(XRD), 7-lithium nuclear magnetic resonance (7Li-NMR),
and density functional theory (DFT) calculations. For both ILCs, the
nematic cybotactic (Ncyb) and smectic A and C mesophases were characterized.
Two organizational monolayer and bilayer regimes for the smectic A
and C mesophases were characterized by the XRD pattern, and the Ncyb
mesophase was assigned by the analysis of the low intensity of the
peak at 2θ = 2.70°, suggesting some smectic character for
the nematic mesophase. A correlation length (ξ) of around 20
layers and 7 layers was established by XRD for the monolayer and bilayer
organization in the SmC mesophase. Single-crystal XRD, 7Li-NMR experiments, and DFT calculations were performed and are discussed
in the context of the LC behavior influenced by the benzyloxy-terminated
group. A model for the layering organization is presented as well
as the organization in the Ncyb, SmA, and SmC mesophases.