Solution- and solid-phase synthesis of components for tethered bilayer membranes

The synthesis of the novel compound PhCH2SS(C24H44N4O10)(C20H41) (5) for the preparation of tethered bilayer membranes is described. The compound is the all-amide analogue of the previously reported ester-containing membrane-forming material PhCH2SS( C24H40O14)(C20H41) (1) The advanced intermediate (C20H41) C16H28N3O8 (17) was prepared from the same starting materials using both solution-phase (13% yield) and solid-phase (81% yield) techniques. Monolayers on gold derived from 5 have been analyzed by ellipsometry and FTIR. The monolayers exhibit thicknesses similar to monolayers derived from 1 and possess H-bonded amide functionality.