A novel class of linear arylamide oligomers has been designed and synthesized from naphthalene-2,7-diamine and benzene-1,3,5-tricarboxylic acid segments. The molecules carry two (tert-butoxycarbonylamino) groups at the ends and one to three hydrophilic N,N-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)amino groups at one side of the backbone. The oligomers self-assembled into vesicular structures in methanol as a result of ordered stacking of the oligomeric amide backbones, which were evidenced by SEM, AFM, TEM, and fluorescent micrography experiments. It was also found that the tert-butoxycarbonylamino groups at the ends played an important role in promoting the ordered stacking of the backbones. Structural factors that affected the self-assembly of the oligomers were investigated. A two-layer model that was supported by TEM has been proposed for the formation of the vesicular structures, which was driven by both the hydrogen bonding and aromatic stacking.

An amphiphilic aromatic amide polymer has been prepared from the condensation of 1,8-naphthalimide-3,6-diamine and isophthalic acid precursors, both of which bear tetraethylene glycol chains. Fluorescence and UV-vis experiments for the polymer and mono-, tri-, penta-, and heptameric control compounds indicate that the polymer can form a helical hollow foldamer in both water and organic solvents of high and low polarity, including N,N-dimethylformamide, methanol, chloroform and dichloromethane. Fluorescence experiments in binary solvents reveal that in benign chloroform or dichloromethane of low polarity, across-layer intramolecular hydrogen bonding is the main driving force for the formation of the helical conformation. In highly polar water and organic solvents like methanol, the solvophobicity is the main driving force. Fluorescence experiments for the corresponding N-methylated polymer indicate that N-methylation reduces the folding propensity of the polymer considerably, but in polar solvents such as methanol, the polymer can still form the helical conformation.

An amphiphilic aromatic amide polymer has been prepared from the condensation of 1,8-naphthalimide-3,6-diamine and isophthalic acid precursors, both of which bear tetraethylene glycol chains. Fluorescence and UV-vis experiments for the polymer and mono-, tri-, penta-, and heptameric control compounds indicate that the polymer can form a helical hollow foldamer in both water and organic solvents of high and low polarity, including N,N-dimethylformamide, methanol, chloroform and dichloromethane. Fluorescence experiments in binary solvents reveal that in benign chloroform or dichloromethane of low polarity, across-layer intramolecular hydrogen bonding is the main driving force for the formation of the helical conformation. In highly polar water and organic solvents like methanol, the solvophobicity is the main driving force. Fluorescence experiments for the corresponding N-methylated polymer indicate that N-methylation reduces the folding propensity of the polymer considerably, but in polar solvents such as methanol, the polymer can still form the helical conformation.