ORGN 185

Creating interlocked molecules through dynamic covalent chemistry

Kirsten Griffiths, nanopower@chem.ucla.edu, Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, CA 90095-1569, Claire R. Yates, cryates@chem.ucla.edu, California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095, Brian H. Northrop, northrop@chem.ucla.edu, Department of Chemistry and Biochemistry and California Nanosystems Institute, University of California, Los Angeles, 607 Charles E. Young Drive East, Box 951569, Los Angeles, CA 90095, Stuart J. Cantrill, California NanoSystems Institute and Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095-1569, and J Fraser Stoddart, stoddart@chem.ucla.edu, Department of Chemistry and Biochemistry, California NanoSystems Institute, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, CA 90095-1569.

Dynamic covalent chemistry (DCC) concerns chemical reactions that are carried out reversibly under equilibration conditions. The reversible nature of such processes introduces the prospects of ‘error-checking' and ‘proof-reading' into synthetic protocols allowing for the efficient formation of highly-organized interlocked molecules. Not only are the reaction products robust, in the sense that they are held together by covalent bonds, but they also remain fluxional as a consequence of the reversible covalent bonds chosen to knit the pieces together. In short, DCC enjoys the best of both worlds, blending the adaptability of supramolecular systems with the inherent stability of covalent bonds. The reversible nature of the carbon-nitrogen double bond found in imines has been exploited for the synthesis (BOX) of many novel topological molecular architectures, employing the simple concept of threading a R2NH2⁺ ion through one monotopic crown ether (dibenzo[24]crown-8), coined ammonium binding. This recognition motif have been utilized extensively in the he building blocks for our molecular meccano kit and has led to more elaborate multiply encircled and/or multiply threaded superstructures. We have developed methodology using stoppering, slippage, or clipping approach for assembling such supermolecules. This poster will discuss the application of DCC to the synthesis of interlocked molecules and interwoven bundle-like supermolecules that have been successfully synthesized using the dialkylammonium ion / crown ether recognition motif in our laboratories.

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

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007