Synthesis and self-assembly properties of the first fluorescein-based hexacatenar mesogens

Abstract

First series of fluorescein-based hexacatenar mesogens consisting of a central fluorescein unit and two 1,2,3-triazole dendritic wings were designed and synthesized by using the Williamson reaction and Cu-assisted alkyne-azide cycloaddition reaction. Polarized optical microscopy textures, differential scanning calorimetry curves, and X-ray diffraction (XRD) data demonstrated that all the compounds can self-assemble into hexagonal columnar mesophases. Organogel test demonstrated that these compounds could form organogel in some moderate polar solvents with irregularly winkled morphologies. Density functional theory calculation demonstrated that these mesogens adopted distorted conformation which might be the reason why narrow mesogenic temperature ranges and irregularly winkled morphologies in these compounds are observed.