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Hydrogen-bonded benzylidenebenzohydrazide macrocycles and oligomers: testing the robust capacity of an amide chain in promoting the formation of vesicles
- Source :
-
Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry . Jul2010, Vol. 51 Issue 29, p3830-3835. 6p. - Publication Year :
- 2010
-
Abstract
- Abstract: This Letter describes 2-(2-(dioctylamino)-2-oxoethyl-amino)-2-oxoethoxyl (DOAOE)-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⋯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. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 00404039
- Volume :
- 51
- Issue :
- 29
- Database :
- Academic Search Index
- Journal :
- Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 51810496
- Full Text :
- https://doi.org/10.1016/j.tetlet.2010.05.076