Synthesis of novel, boron-containing cavitands derived from calix[4]resorcinarenes and their molecular recognition of biologically important polyols in Langmuir films

An efficient synthetic route for the synthesis of cavitands derived from calix[4]resorcinarene and its tetrabromo derivative was elaborated. A large-scale preparation was achieved in excellent yield, by replacing the high-boiling solvents with acetone. The tetrabromocavitands were transformed into tetra-boronic acid cavitands via lithiation with butyllithium and reaction with triethylborate. Two lipophilic cavitands bearing four boronic acid residues were demonstrated to form stable Langmuir monolayers at the water-air interface. These cavitand receptors differ in bridging unit between oxygen atoms, i.e. one contains a one-carbon unit and the other a two-carbon unit. L-sorbose, D-galactose, D-glucose, and D-cellobiose were selected for molecular recognition studies using the Langmuir techniques. The unsubstituted tetra-n-undecyl calix[4]resorcinarene was used as a reference receptor compound. Differences in surface potential were diagnostic of the different types of binding forces, which can occur. (C) 2004 Elsevier Ltd. All rights reserved.