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.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Yun-Xiang
YX
Xu
Gui-Tao
GT
Wang
Xin
X
Zhao
Xi-Kui
XK
Jiang
Zhan-Ting
ZT
Li
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