Diastereomeric cinchona based surfactants: features and chirality expression of their aggregates

The preparation and the aggregation properties of new diastereomeric cationic cinchona derivatized surfactants are described. The opposite configuration of a stereogenic center strongly influences the morphology, the colloidal features, and the chiral recognition capabilities of the diastereomeric aggregates that have been investigated by various physico-chemical tools.

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(1S,2S,4S,5R)-(+)-1-Hexadecyl-5-vinyl-2-quinuclidiniume-methanol bromideC26H50BrNO[α]D25=17.2 (c 4.7, MeOH)

(1S,2R,4S,5R)-(+)-1-Hexadecyl-5-vinyl-2-quinuclidiniume-methanolC26H50BrNO[α]D25=77.9 (c 2.2, MeOH)