CHED 518 |
| We have prepared an amphiphilic catenanes, composed of two interlocked macrocyclic rings serving as a hydrophilic (polar) head and two covalently bound hydrophobic (non-polar) tail. We have used an organic-templated method based on the cyclophane-crown ether complex first prepared by Stoddart and co-workers in 1989. To synthesize our catenane, we reacted a biscationic cyclophane precursor bearing a long hydrophobic chain and two nucleophilic nitrogens with a bis-electrophile (also bearing a long chain) to close the ring, thus forming the electron poor cyclophane unit. This is accomplished in the presence of an electron-rich crown ether to form the amphiphilic catenane. Through aromatic stacking interactions, the cyclophane unit is closed around the crown ether in a one-step synthesis. We are currently investigating supramolecular interactions of this catenane. All intermediates were characterized using 1H NMR and mass spectroscopy. Synthetic details, preliminary colloidal studies, and future work will be presented. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Chemical Education |