Synthesis, Langmuir and Langmuir–Blodgett film behaviour of new dendritic amphiphiles

Abstract

New amphiphilic compounds 1–9 that feature a construction with dendronized hydrophilic and hydrophobic segment groups connected to a specific aromatic or aliphatic spacer unit have been synthesized, following a modular building block strategy. The hydrophilic dendrons are typically branched elements with peripheral carboxylic groups, unlike the hydrophobic dendrons that contain peripheral alkyl chains as part of respective amide functions. The hydrophilic dendrons are in different generations of branching, while the hydrophobic dendrons are all in the first generation of branching (three terminal branching), but differ in the length of the alkyl chains, thus giving rise to designed structure and amphiphilic properties in the new compounds. The resulting surfactants are capable of forming well-defined Langmuir films of remarkable stability when spread from a solution onto an aqueous subphase. Nevertheless, specific packing behaviour and orientation of the amphiphilic molecules were found, depending on the molecular structure, as determined using analysis of the surface pressure–area (π–A) isotherms. Langmuir–Blodgett transfer of the first monolayer from a pure water subphase to a clean silicon wafer proved possible for the amphiphiles of peripheral alkyl chain length C12, while the amphiphiles with the longer alkyl chains failed, possibly due to the more rigid monolayers they form, impeding the transfer.