First isoflavone-based hexacatenar derivatives with columnar liquid crystalline self-assembly and binding selectivity behavior

Abstract

ABSTRACT The incorporation of different functional groups into organic molecules is a common method to construct soft liquid crystalline materials with multiple properties and adjust mesophases from one-dimensional to three-dimensional structures. This article reports the synthesis, characterization, self-assembly, and binding selectivity behaviors of the first isoflavone-based hexacatenar liquid crystalline materials with an isoflavone as central rigid core and two 1,2,3-triazole dendritic wings as terminal functional units. Polarized optical microscopy, differential scanning calorimetry, and small-angle X-ray scattering (SAXS) investigations indicated that all the compounds could self-assemble into rectangular columnar mesophase. The differences in temperature range of mesophase and sequence of mesophase compared with previously reported coumarin-based polycatenars were attributed to the change of position of carbonyl. The optical spectra indicated that these compounds display selectivity for Fe2+ among the different and cations. FT-IR and density functional theory calculations before and after interaction with Fe2+ were employed to demonstrate the recognition sites. The design strategy here provides a simple method to construct supramolecular self-assembly materials with wide properties and potentials.