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First Room Temperature Chiral Anionic Liquid Forming Micelles and Reverse Micelles
Vijay Raghavan1, Prasad L Polavarapu1
1Department of Chemistry, Vanderbilt University , Nashville, Tennesse 37235, United States.
The Journal of Physical Chemistry. B
|January 26, 2017
Summary
We synthesized the first fully chiral, surface-active ionic liquid (IL) from tartaric acid. This novel IL exhibits unique properties, including self-assembly into chiral micellar aggregates in various solvents.
Area of Science:
- Materials Science
- Supramolecular Chemistry
- Green Chemistry
Background:
- Ionic liquids (ILs) are salts that are liquid at room temperature, with diverse applications.
- Chirality is crucial in many chemical and biological processes, but chiral ILs are less explored.
- Surface-active ILs combine properties of surfactants and ILs, offering unique functionalities.
Purpose of the Study:
- To synthesize and characterize the first fully chiral, surface-active ionic liquid (T12M).
- To investigate the unusual properties and self-assembly behavior of T12M.
- To explore the potential of biodegradable tartaric acid as a precursor for novel ILs.
Main Methods:
- Synthesis of T12M from biodegradable tartaric acid.
- Characterization of T12M's physical properties, including its phase behavior and melting point.
- Investigation of T12M's solubility and self-assembly in hydrogen-bonding (water) and non-hydrogen-bonding (chloroform) solvents using techniques to determine micellar aggregate structures and concentrations.
Main Results:
- T12M is the first fully chiral, surface-active ionic liquid, derived from tartaric acid.
- T12M exhibits unique phase behavior, existing as a room temperature IL for 3 days before transforming into a semi-solid with a melting point of ~55 °C.
- T12M forms chiral micellar aggregates (CMAs) and reverse-CMAs in water and chloroform at very low concentrations, with structures ranging from spherical to lamellar.
Conclusions:
- Biodegradable tartaric acid is a viable and unconventional precursor for synthesizing advanced ionic liquids.
- T12M possesses a unique combination of chirality, surface activity, and tunable self-assembly, opening new avenues for chiral materials.
- The ability of T12M to form chiral micellar aggregates in diverse solvents highlights its potential in areas requiring chiral recognition and separation.
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