Preparation and characterization of bottle-brush polymer via host−guest self-assembly between β-cyclodextrin and adamantane



Supramolecular assemblies with a bottle-brush structure are obtained by inclusion complexation between β-cyclodextrin and adamantane. β-cyclodextrin-modified chitosan is synthesized via the aldimine condensation reaction between β-cyclodextrin monoaldehyde and chitosan as the host. The guest is prepared through the esterification reaction between methoxypoly(ethylene glycol) and 1-adamantanecarboxylic acid chloride. The supramolecular assemblies are formed through the inclusion of adamantane-modified methoxypoly(ethylene glycol) into the β-cyclodextrin cavity on the chitosan chain. Fourier transform infrared and 1H NMR spectra were used to prove that the host, guest and assemblies were successfully obtained. UV−visible spectra were employed to confirm the formation of assemblies. Furthermore, the size of the particles in the assembled solution, the change before and after self-assembly, and the effect of the addition of competitive molecules were studied by dynamic light scattering measurements. The results indicate that supramolecular assemblies have formed successfully which might be used to realize the biomimetic structure of the articular cartilage proteoglycan. © 2014 Society of Chemical Industry