β-Cyclodextrin induced hierarchical self-assembly of a cationic surfactant bearing an adamantane end group in aqueous solution

Abstract

A cationic surfactant with adamantane as the end group, 1-[11-((adamantane-1-carbonyl)oxy)-undecyl]pyridinium bromide (AP), has been synthesized. Its β-cyclodextrin (β-CD) induced hierarchical self-assembling behaviors in aqueous solution were investigated using transmission or scanning electron microscopy methods and small-angle X-ray scattering measurements. Like conventional single chain surfactants, micelles could be formed by AP itself in dilute solutions. However, the dramatic phase transitions of these micelles occurred when host–guest inclusions between AP and β-CD were sequentially produced at different host/guest molar ratios (R), corresponding to the supramolecules with different chemical structures. The AP micelles could be changed into spherical unilamellar vesicles by adding β-CD to reach an R value of 1 : 1. Such vesicles then evolved into multi-wall nanotubes or hydrogels when the β-CD amount was further increased to obtain an R value of 2 : 1. The unique structural characteristics of these supramolecular aggregates come from their “monolayer-like” walls, which have rarely been reported in the past for CD/surfactant inclusion complexes. The interesting results obtained here not only enrich the β-CD/surfactant aggregation systems, but also provide a novel and facile strategy to tune the morphology and structure of aggregates.