Self-assembly of vesicles from amphiphilic aromatic amide-based oligomers.
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.
Xu
Yun-Xiang
YX
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Wang
Gui-Tao
GT
Zhao
Xin
X
Jiang
Xi-Kui
XK
Li
Zhan-Ting
ZT
D000577:Amides / Q000737:chemistry*; D004247:DNA / Q000737:chemistry; D006860:Hydrogen Bonding; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D018625:Microscopy, Atomic Force / Q000379:methods; D008855:Microscopy, Electron, Scanning / Q000379:methods; D046529:Microscopy, Electron, Transmission; D008856:Microscopy, Fluorescence / Q000379:methods*; D008956:Models, Chemical; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013499:Surface Properties
D000577:Amides; D011108:Polymers; D012997:Solvents; D004247:DNA; D000432:Methanol