Functionalized double-chain surfactant 1 (potassium O,O
‘-didodecylphosphorodithioate) was synthesized.
Its small unilamellar vesicles were characterized by dynamic laser light scattering and differential scanning
calorimetry and its giant vesicles by phase-contrast optical microscopy. Also, 1's giant vesicles containing
fluorescent dye 4a (5-carboxyfluorescein) or 4b [5-(dodecanamido)fluorescein] were characterized by
epifluorescence microscopy. In a pH 9.0 borate buffer at 25 °C, vesicular 1 reacted with 2 (2-chloroethyl
phenyl sulfide), a simulant for the chemical warfare agent mustard [bis(2-chloroethyl) sulfide], to give 5
[S-[(2-phenylthio)ethyl] O,O‘-didodecylphosphorodithioate], involving capture of reactive intermediate cation
9 (1-phenylthiocyclopropane) by the anion of 1. This reaction was accompanied by the precipitation of 5,
which resulted in wounding/destruction of the vesicles and the release of dye 4a (from giant vesicles). The
combination of the conversion of 2 into 5 and dye release suggests the potential of vesicular systems for
simultaneous decontamination and signaling of chemical agents. 2 hydrolyzed to give only 6 [2-(phenylthio)ethanol] in the pH 9.0 buffer at 25 °C.
All of the stereoisomeric forms of the surfactant, sodium
3-[2-methyl-4,5-bis(hexadecyloxymethyl)-1,3-dioxolan-2-yl]propane-1-sulfonate, have been prepared: the
enantiomers (+)-1 and (−)-1, the
racemate
(±)-1 (by two different methods), and meso
2 and meso
3. Vortexed vesicles
of these materials were
characterized by dynamic laser light scattering, to give vesicle sizes,
and by differential scanning calorimetry,
to give bilayer phase transition temperatures and associated
enthalpies. Different calorimetry results
were obtained for (+)-1 [(−)-1],
(±)-1, 2, and 3. In particular,
a comparison of the results for (+)-1
[(−)-1]
and (±)-1 indicated the operation of enantiomer
discrimination. The criteria of the “absolute” method
of
stereochemistry applied to this study were not completely
fulfilled.
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