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Synthesis of Calamitic Fluorinated Mesogens with Complex Crystallization Behavior.

Denis Anokhin^1,2, Alina Maryasevskaya¹, Ainur Abukaev¹

¹Faculty of Chemistry, Lomonosov Moscow State University, GSP-1, 1-3 Leninskiye Gory, 119991 Moscow, Russia.

Molecules (Basel, Switzerland)

|December 23, 2023

Summary

Researchers synthesized a novel fluorinated mesogen, a model for perfluorosulfonic acid (PFSA) membranes. Its self-organization and thermal transitions are key for creating aligned channels in membrane fabrication.

Keywords:

DSC fluorinated compounds liquid crystals melting point smectic

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Area of Science:

Materials Science
Supramolecular Chemistry
Polymer Science

Background:

Perfluorosulfonic acid (PFSA) membranes are crucial for various electrochemical applications.
Understanding the self-organization of molecular precursors is vital for controlling membrane structure and function.
Fluorinated mesogens offer unique properties for designing advanced materials.

Purpose of the Study:

To synthesize and characterize a novel fluorinated mesogen as a model compound for PFSA membranes.
To investigate the self-organization behavior and thermal transitions of the synthesized mesogen.
To establish the relationship between molecular self-organization and channel alignment in membrane fabrication.

Main Methods:

Multi-step organic synthesis to obtain the target fluorinated mesogen.
Differential scanning calorimetry (DSC) and polarized optical microscopy to study thermal behavior.
X-ray diffraction (XRD) to determine crystalline structures and unit cell models.
Molecular dynamics simulations to correlate thermal transitions with molecular orientation.

Main Results:

Successful synthesis of 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-4-iodobutoxy)ethanesulfonic acid with 78% overall yield.
Observed crystal-to-crystal transition at 150 °C and isotropization at 218 °C.
Formation of smectic liquid crystalline phases upon cooling, transitioning to a layered crystal phase with alternating hydrophilic and hydrophobic layers.
Proposed crystalline unit cell models at room temperature and 170 °C using XRD.
Simulations confirmed that thermal transitions are linked to a loss of molecular orientation.

Conclusions:

The synthesized fluorinated mesogen exhibits complex thermotropic behavior and self-organization capabilities.
The study highlights the critical role of precursor self-organization in achieving aligned channels for membrane fabrication.
This model compound provides insights into the fundamental principles governing the structure-property relationships in PFSA materials.