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Updated: Jun 26, 2026

Controlling the Size, Shape and Stability of Supramolecular Polymers in Water
Published on: August 2, 2012
Effect of headgroup chirality in nanoassemblies. Part 1. Self-assembly of D-isoascorbic acid derivatives in water
Moira Ambrosi1, Pierandrea Lo Nostro, Emiliano Fratini
1Department of Chemistry and CSGI, University of Florence, 50019 Sesto Fiorentino (Firenze), Italy.
Abstract:
L-(+)-Ascorbic acid and D-(-)-isoascorbic acid are epimers, with an opposite configuration at the C5 stereogenic chiral center. Single-chained surfactants that carry a L-ascorbic or d-isoascorbic acid residue as hydrophilic headgroup and an alkanoate tail as hydrophobic chain were synthesized. We refer to these as L-ASCn and D-ASCn, with n=8, 10, or 12. The role of the headgroup configuration in determining the nature of both the pure compounds and their nano assembly in aqueous dispersions were studied. Surface tension, infrared spectroscopy, differential scanning calorimetry, conductivity, small-angle X-ray scattering, and wide-angle X-ray diffractometry were used to characterize surfactant properties as a function of temperature and concentration. The L and D headgroup forms have significantly different hydration. This greatly affects the structure and stability of the aggregates in the micellar and coagel states.
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