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.

Keywords:

• Fluorescein
• hexacatenar
• liquid crystal
• organogel

Acknowledgments

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

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by China West Normal University Doctor Startup Fund (No. 412821), Major project funds of Chemical Synthesis and Pollution Control Key Laboratory of Sichuan Province (No. CSPC202101), The Science and Technology Department of Sichuan Province (No. 2022NSFSC1237), Natural Science Foundation of China (No. 22265030), and Funds for leading local scientific technological development by the central government (202307AB110010).