Self-assembly of chiral bicyclic keto-alcohols into supramolecular helices in the solid state

Abstract

The bicyclic keto-alcohol (1S,4R,6S)-bicyclo[2.2.2]octan-6-ol-2-one, (+)-3, self-assembles in the solid state through hydrogen bonds between the alcohol and the carbonyl groups creating supramolecular helices, without the aid of other forces such as π–π interactions to stabilise the superstructure. Furthermore, the bicyclic compound (4) although structurally quite different, in relation to (+)-3, also formed a supramolecular helix in a similar fashion.