Divalent binding of a bis(adamantyl)-functionalized calix[4]arene to beta-cyclodextrin-based hosts: an experimental and theoretical study on multivalent binding in solution and at self-assembled monolayers.

The divalent binding of a bis(adamantyl)-functionalized calix[4]arene (1) to an EDTA-tethered beta-cyclodextrin (CD) dimer (2) in solution (1.2 x 10(7) M(-)(1)) was 3 orders of magnitude weaker than the binding constant ( approximately 10(10) M(-)(1)) for the interaction of 1 at CD self-assembled monolayers (SAMs) on gold. This difference in binding is rationalized using a theoretical model, which interprets the divalent binding as two consecutive monovalent binding events, i.