Premium
Host–Guest Chemistry of Carboranes: Synthesis of Carboxylate Derivatives and Their Binding to Cyclodextrins
Author(s) -
Nekvinda Jan,
Grüner Bohumír,
Gabel Detlef,
Nau Werner M.,
Assaf Khaleel I.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201802134
Subject(s) - moiety , chemistry , supramolecular chemistry , host–guest chemistry , carborane , aqueous solution , binding affinities , molecule , carboxylate , inclusion compound , stereochemistry , affinities , combinatorial chemistry , cyclodextrin , polymer chemistry , organic chemistry , biochemistry , receptor
Polyhedral carboxymethyl carborane (C 2 B 10 H 12 ) derivatives, including mono‐ and disubstituted o ‐, m ‐, and p ‐isomers, have been synthesized. Supramolecular host–guest complexation of these derivatives with cyclodextrins (CDs; namely, α‐, β‐, and γ‐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 β‐CD.