Hydrogen bonded aromatic hydrazide foldamers for the self-assembly of vesicles and gels

This paper describes an investigation of the structural and side-chain factors for the formation of vesicles and gels by hydrogen bonding-mediated aromatic hydrazide foldamers. Six foldamers; and one straight analog that bear discrete side chains have been synthesized. SEM and AFM studies reveal that the molecules with the appended 2-(2-(dialkyl-amino)-2-oxoethylamino)-2-oxoethoxyl chains form vesicles, hydrogels or organogels, depending on the solvents. Both the inner amide units and the terminal N,N-dialkylamide units in the chains are revealed to play essential roles in controlling the self-assembly. The former facilitates it by forming the intermolecular hydrogen bonding, while the latter modulates it by providing solubility and balancing the hydrophobicity of the whole molecules in solvents of varying polarity. (C) 2009 Elsevier Ltd. All rights reserved.