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Development of New D,L-Methionine-based Gelators
Shunichi Suga1, Masahiro Suzuki2, Kenji Hanabusa2,3
1Faculty of Textile Science & Technology, Shinshu University.
Journal of Oleo Science
|May 1, 2018
Summary
New gelators based on D,L-methionine were synthesized and tested. The oligo(dimethylsiloxane)-containing gelators, particularly DL-Met-R18/Si7-8, showed enhanced ability to form stable gels in various solvents.
Area of Science:
- Supramolecular Chemistry
- Materials Science
- Organic Synthesis
Background:
- D,L-Methionine serves as a versatile starting material for novel compound synthesis.
- Developing effective gelators is crucial for applications in various chemical and material sciences.
- Oligo(dimethylsiloxane) moieties can be incorporated to modify gelator properties.
Purpose of the Study:
- To synthesize and characterize a new gelator, N-10-undecenoyl-D,L-methionylaminooctadecane (DL-Met-R18).
- To prepare and evaluate oligo(dimethylsiloxane)-containing derivatives (DL-Met-R18/Si3, DL-Met-R18/Si7-8, DL-Met-R18/Si14-15) as gelators.
- To investigate the gelation abilities, thermal stabilities, and structural properties of these new gelators.
Main Methods:
- Synthesis of DL-Met-R18 via modification of D,L-Methionine.
- Preparation of oligo(dimethylsiloxane)-containing gelators using hydrosilylation reactions.
- Gelation tests in nine different solvents to determine minimum gel concentration.
- Characterization using FT-IR spectroscopy, transmission electron microscopy, and rheology measurements.
Main Results:
- DL-Met-R18 showed limited gelation ability, crystallizing in most solvents.
- DL-Met-R18/Si7-8 emerged as the most effective gelator, gelling eight solvents at low concentrations.
- Gelator performance order: DL-Met-R18/Si7-8 ≈ DL-Met-R18/Si14-15 > DL-Met-R18/Si3 >> DL-Met-R18.
- Oligo(dimethylsiloxane) derivatives formed stable gels with mixed solvent systems, with DL-Met-R18/Si7-8 producing transparent/translucent gels.
- FT-IR and TEM confirmed hydrogen bonding and 3D network formation as key to gelation.
Conclusions:
- Incorporation of oligo(dimethylsiloxane) chains significantly enhances the gelation properties of DL-Met-R18.
- DL-Met-R18/Si7-8 is a highly efficient gelator for a wide range of solvents and solvent mixtures.
- Hydrogen bonding and self-assembly into 3D networks are critical for the observed gelation phenomena.
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