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

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.

KEYWORDS:

• Liquid crystal
• chemosensor
• hexacatenar
• isoflavone
• triazole

Acknowledgments

We thank beamline 1W2A at Beijing Synchrotron Radiation Facility (BSRF), China.

Disclosure statement

No potential conflict of interest was reported by the author(s).

Additional information

Funding

This work was supported by the major project fund of Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province (CSPC202101), The Science and Technology Department of Sichuan Province (2022NSFSC1237), and the Talent Program of China West Normal University (17YC019).