Resorcinarene bis-crown silver complexes and their application as antibacterial Langmuir–Blodgett films

Abstract

Silver complexes of a cation binding supramolecular host, resorcinarene bis-crown (CNBC5) with propyl, nonyl, decyl and undecyl alkyl chains were investigated by NMR titration, picrate extraction and single crystal X-ray diffraction. Binding studies showed that both 1 : 1 and 1 : 2 (host–Ag⁺) complexes are present in solution with only a slight effect of the lower rim alkyl chain length on the binding constants (log K 4.0–4.2 for 1 : 2 complexes). Solid state complexes of the resorcinarene bis-crowns bearing either C₃ or C₁₁ chains were obtained. Single crystal X-ray analyses showed that both derivatives bind silver ions by metal–arene and Ag⋯O coordination from the crown ether bridges and from the solvent, and pack in layered or bilayered fashion. Furthermore, the amphiphilic nature of C11BC5 was demonstrated using the Langmuir balance technique. Langmuir–Blodgett films of the amphiphilic C11BC5–Ag complex were transferred onto a substrate and shown to possess antibacterial activity against E. coli.