Chiral Discrimination in Monolayer Packing of Hexade-Canol-Thiophosphoryl-2-Phenylglycinol with two Chiral Center in the Polar Head-Group
The four possible stereomers of a chiral surfactant with two asymmetric centers within the polar head group have been synthesized and their absolute configuration determined by X-ray diffraction. One of the diastereomers exhibits a chiral discrimination when spread on water interface: the monolayer racemic film undergoes a phase transition from a liquid-expanded towards a liquid-condensed phase upon compression, while the pure enantiomers only have a liquid-expanded phase, as revealed by the measured pressure-area isotherms. The transition pressure-composition diagram indicates that heterochiral interactions are favored. Our results are compared to predictions of Andelman and de Gennes1 based upon a statistical model.
KeywordsSurfactant Glycerol Sulfuric Acid Calorimetry Phosphatidylcholine
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