Induction of an Infinite Periodic Minimal Surface by Endowing An Amphiphilic Zwitterion with Halogen-Bond Ability.

We have designed an amphiphilic zwitterion with an iodine-substituted imidazolium cation. Although it forms a layered assembly with flat interfaces, the addition of an equimolar amount of bis(trifluoromethane)sulfonimide results in the formation of a bicontinuous cubic liquid-crystalline assembly with a primitive-type infinite periodic minimal surface, where its zwitterionic headgroup sits regularly. IR measurements revealed that halogen bond between the iodine atoms on the imidazolium cation and the anions is involved in its molecular-assembly behavior. The present results clearly indicate the potential utility of halogen bonding to control the dimensionality and continuity of the ionic/nonionic interface of amphiphiles in bulk and consequent mesophase patterns, which may be a significant new molecular technology for precisely arranging functional molecules on a 3D continuous interfaces.