Synthesis of Calix[4]arene Derivatives Containing a Nucleobase and their Interaction with Complementary Nucleosides at the Air–Water Interface

Abstract

Amphiphilic calix[4]arene derivatives with a nucleobase on the lower rim have been synthesized in good yields by the condensation of calix[4]arenediamine {5,11,17,23-tetra-tert-butyl-25,27-bis(2-aminoethoxy)-26,28-dihydroxycalix[4]arene} with uracilo-N-acetic acid, thymino-N-acetic acid and adenino-N-propionic acid in the presence of CDI in DMF. Monolayers of the amphiphilic calix[4]arene-nucleobase derivatives on the surface of pure water, the aqueous subphases containing complementary nucleosides, were studied by film balance measurement and relaxation experiments. LB films deposited from all subphases were investigated by UV spectra and FT-IR spectroscopy. All the results indicate that the interaction between the nucleobases in the headgroup of amphiphilic p-tert-butylcalix[4]arene derivatives and the complementary nucleosides in the subphase takes place through multiple hydrogen bonding and the nucleosides can be transferred to solid substrates along with their monolayers.