Assemblies of aziridinemethanols

Two novel long chain aziridinemethanols (1b, c) are described and their mol ecular organisation in the bulk and self-assembling properties in aqueous d ispersion are reported. The orientation of the NH hydrogen of the aziridine alcohol moiety in 1b can be changed by introducing a methyl substituent int o the rigid three-membered ring, leading to a change in the hydrogen bondin g pattern interconnecting these molecules. This change in configuration lea ds to marked differences in the ordering of these molecules in the solid st ate. Although compounds 1b and 1c both form highly organised structures in aqueous media and on the air-water interface, noteworthy differences are ob served. Compound 1c yields left-handed helical ribbons whereas no chiral ag gregates are found for 1b. However, the addition of 2-acetoxybenzoic acid ( aspirin) to an aqueous dispersion of 1b leads to the generation of both lef t- and right-handed helical structures. Under these conditions a reaction h ad taken place that was specific for the ortho-isomer of acetoxybenzoic aci d.