Hydrogen-bonded benzylidenebenzohydrazide macrocycles and oligomers: testing the robust capacity of an amide chain in promoting the formation of vesicles
作者:Ben-Ye Lu、Guang-Jun Sun、Jian-Bin Lin、Xi-Kui Jiang、Xin Zhao、Zhan-Ting Li
DOI:10.1016/j.tetlet.2010.05.076
日期:2010.7
This Letter describes 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl (DPAOE)-tuned self-assembly of vesicles from rigid macrocycles and foldamer-like oligomers. The molecules are prepared through the formation of reversible hydrazone bonds from aldehyde and benzo-hydrazide precursors, which are further facilitated by intramolecular N center dot center dot center dot H-O hydrogen bonding. SEM. AFM, and fluorescent encapsulation studies reveal that the molecules all self-assemble into vesicular structures in methanol, while similar molecules bearing the triethylene glycol or n-decyl chains do not. The results illustrate that DOAOE is robust in promoting the formation of vesicles for aromatic Systems in polar solvents. (C) 2010 Elsevier Ltd. All rights reserved.