Adamantyl-terminated dendronized molecules: synthesis and interaction with β-cyclodextrin-functionalized poly(dimethylsiloxane) interface

Abstract

The supramolecular interaction between the host molecule β-cyclodextrin (β-CD) and the guest molecule adamantane is extensively applied in several disciplines. However, recent studies on the applications of this molecular recognition mainly focused on glass, silicon, and gold substrates. Few studies have explored the field of poly(dimethylsiloxane) (PDMS), an optically transparent elastomer widely used in biological microfluidic devices. In the present study, various functional group-modified adamantyl-terminated dendronized molecules were synthesized via an efficient and facile route. The binding of adamantyl-terminated dendronized molecules onto β-CD-conjugated PDMS surfaces and their reversible dissociation from PDMS surfaces through the competitive mechanism of β-CD-N₃ were studied. The results showed that the dissociation is relatively slow compared with the binding, and the former process can be accelerated through exchanging the original β-CD-N₃ solution with a fresh one. Afterward, more complex multilayer assemblies were constructed on PDMS surfaces using the host–guest interaction between adamantane and β-CD as well as between biotin and streptavidin. A further study on the association and dissociation of the established multilayer assemblies showed that the assembly constructed with a biotinylated monoadamantyl-terminated molecule has a reversible property, whereas that with a biotinylated triadamantyl-terminated molecule has an irreversible property. These results demonstrated that the reversible properties of the fabricated assembly can be easily modulated on the PDMS surfaces by regulating the valence of the supramolecular interaction between adamantane and β-CD.