Symmetric and Asymmetric Bolaamphiphiles from Ascorbic Acid

The properties of novel bolaamphiphiles that carry epimers of vitamin C (l-ascorbic acid and/or d-isoascorbic acid) as hydrophilic head groups, and an interconnecting aliphatic C12 chain (DD, DL, and LL) were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA),...

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Bibliographic Details
Published in:The journal of physical chemistry. B 2011-10, Vol.115 (40), p.11638-11649
Main Authors: Dolle, Christian, Magrone, Pietro, Riva, Sergio, Ambrosi, Moira, Fratini, Emiliano, Peruzzi, Niccolò, Nostro, Pierandrea Lo
Format: Article
Language:English
Subjects:
Ascorbic Acid - chemistry
B: Surfactants, Membranes
Differential scanning calorimetry
Dispersions
Fourier transforms
Furans - chemistry
Heating
Hydrogen Bonding
Infrared spectroscopy
Nanostructure
Phase transformations
Pyridones - chemistry
Surface-Active Agents - chemistry
Surfactants
Temperature
Thermodynamics
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Summary:The properties of novel bolaamphiphiles that carry epimers of vitamin C (l-ascorbic acid and/or d-isoascorbic acid) as hydrophilic head groups, and an interconnecting aliphatic C12 chain (DD, DL, and LL) were investigated by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), small-angle X-ray scattering (SAXS), X-ray diffraction (XRD), and Fourier transform infrared spectroscopy (FTIR) in the solid state (anhydrous powders) and in aqueous dispersions as a function of the surfactant concentration. Upon heating, the aqueous dispersions undergo a phase transition from a hydrated semicrystalline “coagel” to a micellar phase. The results suggest that the headgroup chirality determines the formation of either inter- or intramolecular hydrogen bonds between the polar heads, which affect the phase behavior and structural properties of the nanoassemblies produced by these surfactants in water dispersions. The DSC data of aqueous dispersions were analyzed to obtain the size distribution of the pores in the coagel state.
ISSN:1520-6106
1520-5207
DOI:10.1021/jp204920y