Assemblies of aziridinemethanols

Abstract

Two novel long chain aziridinemethanols (1b, c) are described and their molecular organisation in the bulk and self-assembling properties in aqueous dispersion are reported. The orientation of the NH hydrogen of the aziridinealcohol moiety in 1b can be changed by introducing a methyl substituent into the rigid three-membered ring (1c), leading to a change in the hydrogen bonding pattern interconnecting these molecules. This change in configuration leads to marked differences in the ordering of these molecules in the solid state. Although compounds 1b and 1c both form highly organised structures in aqueous media and on the air–water interface, noteworthy differences are observed. Compound 1c yields left-handed helical ribbons whereas no chiral aggregates are found for 1b. However, the addition of 2-acetoxybenzoic acid (aspirin) to an aqueous dispersion of 1b leads to the generation of both left- and right-handed helical structures. Under these conditions a reaction had taken place that was specific for the ortho-isomer of acetoxybenzoic acid.