"Host-guest complexes of cyclodextrins and nanodiamonds as strong non-covalent binding motif for self-assembled nanomaterials"

Frauke Schibilla: Voskuhl J, Fokina NA, Dahl JEP, Schreiner PR, Ravoo BJ; Chemistry , 11/17/17.

Additional Authors: Voskuhl J, Fokina NA, Dahl JEP, Schreiner PR, Ravoo BJ

Abstract:

We report on the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane and triamantane by β- and γ-cyclodextrin (β-CD and γ-CD) with particularly suited hydrophobicity and symmetry for an optimal fit of host and guest. We studied the host-guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity but 1:2 association for the largest ND in the series (triamantane) with β-CD. We found higher binding affinities of carboxy-substituted NDs compared to amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with D-mannose using adamantane, diamantane, and triamantane as non-covalent anchors and compared in agglutination experiments with the lectin concanavalin A (ConA). Agglutination is directly correlated to the host-guest association: adamantane showed a lower agglutination than di- and triamantane with β-CDV and almost no agglutination with γ CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.