ORGN 181 |
| Electrochemically switchable mechanically interlocked molecules incorporating cyclobis(paraquat-p-phenylene) (CBPQT4+) have found applications as molecular actuators and in molecular electronics. The synthesis of CBPQT4+-containing compounds, however, has been limited to “clipping” strategies because of the sensitivity of the CBPQT4+ ring toward many bases and nucleophiles. Higher yielding and more versatile syntheses of mechanically interlocked compounds will allow the development of new interlocked molecular architectures and applications. Because of its excellent functional group compatibility and mild reaction conditions, we hypothesized that the Cu(I)-catalyzed 1,3-cycloaddition of organic azides and alkynes might be utilized (Scheme 1) to stopper CBPQT4+ pseudorotaxanes efficiently. This alternative methodology complements the clipping approach, and allows template-directed synthesis of [2], [3], and [4]rotaxanes in excellent yields. The efficient synthesis of more complex mechanically interlocked compounds containing CBPQT4+ will be described, as well as the possibilities of integrating these molecules to form higher order molecular machines utilizing this synthetic methodology.
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Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
