Synthesis and characterization of nonlinear coumarin-functionalized liquid crystals incorporating chalcone and ester linkages

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In this study, we have synthesized coumarin functionalized compounds based on benzoate/chalcone (h1–h4) and cinnamate/chalcone (i1–i4) linking group with variable alkoxy side chain. Their molecular structures were determined using spectroscopic techniques such as FT-IR, Mass, 1H NMR, and 13C NMR techniques. The liquid crystalline properties of these compounds were preliminary examined by polarizing optical microscopy study and further confirmed by differential scanning calorimetry studies. In both type of compounds, the compounds with shorter alkyl chains (n = 6, 8) exhibited a nematic phase, while those with longer alkyl chains (n = 10, 12) displayed a smectic C phase. All eight derivatives displayed enantiotropic type mesophase with broad temperature range and high thermal stability. Further, the density functional theory (DFT) calculations were performed for both benzoate/cinnamate based compounds to elucidate the reactivity and electronic properties. Additionally, the structure-property relationship was investigated to understand the effect of the linking group and varying alkyl side chains on the liquid crystalline properties.

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