ORGN 753 |
| Wurster's crowns are a novel class of redox-active macrocyclic receptors based on the incorporation of a phenylenediamine subunit within a macrocyclic framework. In the traditional crown ether topology, a macrocyclic N atom critical to the electrochemical activity of the redox center serves to directly coordinate cationic guests giving rise to strong mutual interactions between the host and guest. However, by altering the macrocyclic architecture, such that both N atoms of the phenylenediamine subunit are contained within the macrocycle, an alternate mode of interaction between the redox center and cationic guest becomes possible through the electron rich p-face of the phenylenediamine subunit. Herein, we utilize a macrobicyclic cryptophane to assess the ability of the electron rich p-face of the phenylenediamine subunit to interact with cationic guests. We, thus, describe general synthetic methods, electrochemical properties and the coordination chemistry of a redox-switchable Wurster's cryptophane and demonstrate both structurally and spectroscopically intimate cation-p interactions. |
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Total Synthesis, Materials, Molecular Recognition, Process R&D, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 13 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |