Host-Guest Chemistry of Carboranes: Synthesis of Carboxylate Derivatives and Their Binding to Cyclodextrins
2018
Abstract
Polyhedral carboxymethyl carborane (C2B10H12) derivatives, including mono- and disubstituted o-, m-, and p-isomers, have been synthesized. Supramolecular host-guest complexation of these derivatives with cyclodextrins (CDs; namely, alpha-, beta-, and gamma-CD) has been investigated in water.
The globular structure of the carborane binding moiety and its hydrophobic character qualify it as an ideal recognition site to form stable inclusion complexes with macrocyclic host molecules in aqueous solution. The measured binding affinities for the carborane derivatives were in the millimolar range (K-a=10(3)-10(4)m(-1)) with differently sized CDs, and preferential binding to beta-CD.