A biocompatible surfactant with folded hydrophilic head group: Enhancing the stability of self-inclusion complexes of ferrocenyl in a β-cyclodextrin unit by bond rigidity

This work reports a new biocompatible surfactant structure, of which the hydrophilic head group is composed of a folded, stable self-inclusion complex of a ferrocenyl substituted β-cyclodextrin (βCD). While multiple intra- or intermolecular complexes can exist for this amphiphile, the molecule folds into a unique intramolecular complex with well-defined conformation, in which part of the aliphatic chain and the ferrocene group are both included in the annular cavity of βCD. Study of different isosteric covalent linkages indicates that this folded structure is stable against displacement by the presence of other small guest molecules. Furthermore, in contrast to ferrocene-CD conjugates that are without the aliphatic chain, the presence of small guest molecules in solution does not influence at all the induced circular dichroism signal of this amphiphile, indicating a sterically congested, but stable, folded conformation of the inclusion complex. This new amphiphile is surface active and, more importantly, does not denature the membrane protein bacteriorhodopsin. Finally, because this surfactant forms self-assembled aggregates, this work introduces a folded structure into soft matters formed by amphiphiles in water.