Long-chain-linked β-cyclodextrin dimers: Synthesis and relationship between reactivity and inclusion complex formation

• Long-chain-linked cyclodextrin dimers show weak self-inclusion complexation.
• Self-inclusion complexes are formed spontaneously in monosubstituted cyclodextrins.
• Comparison of self-inclusion of cyclodextrin monomers and dimers.

We synthesized ditopic compounds bearing two β-cyclodextrin moieties linked by long aryl-alkyl linkers. The process of linker inclusion into β-cyclodextrin cavity was observed during Sharpless click-chemistry conjugation. The target cyclodextrin dimers exhibit self-complexation via a glucose unit inversion phenomenon that is significantly weaker as compared with earlier reported analogs. It was confirmed that both cavities of such cyclodextrin dimers are available for interaction with larger guest molecules.