Modular synthesis of dendritic ionic triphiles and their behavior in three-phase liquid–liquid–liquid system

Triphiles are a narrow group of substances exhibiting unique properties due to the presence of three incompatible parts of the molecule (domains) – oleophilic, hydrophilic, and fluorophilic. For example, triphilic ionic liquids form fascinating crystalline lattices, and triphilic copolymers form micelles with a compartmentalized lipophilic core, which allows them to deliver two different drugs at once and, in addition, be observable in the human body by advanced ¹⁹F magnetic resonance imaging. In our laboratories, we have prepared a broad series of novel triphiles using a sophisticated modular synthesis procedure and we are the first to study these types of compounds in a three-phase toluene/water/perfluoro(methylcyclohexane) system. We have been able to cover the range from completely hydrophilic through oleophilic to fluorophilic, including water-toluene and toluene-fluor amphiphiles, but obtaining a triphile that distributes to all three phases in similar amounts is still a subject of further research. However, we have mapped the effect of the size of individual domains on the overall affinity of the molecule. In addition, we were able to obtain a compound that forms the aforementioned multicompartment micelles, and some of our triphiles were also able to simultaneously emulsify both toluene with water and water with perfluoro(methylcyclohexane).

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• Baka M., Edr A.*, Krupková A.*, Červenková  Šťastná L., Bernášková J., Greguš V., Čermák J., Strašák T.: Modular synthesis of dendritic ionic triphiles and their behavior in three-phase liquid–liquid–liquid system. J. Mol. Liq. 2024, 404, 124920. doi.org/10.1016/j.molliq.2024.124920