A Facile Route to New and Old Cyclophanes from a Pnictogen-activated Self-Assembly Reaction

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The well-defined topology and high strain of cyclophanes has found utility in a number of applications including asymmetric catalysis, insulating plastics, and organic electronics.  Unfortunately, the field of cyclophane chemistry has been hindered by a lack of high yielding and functional group tolerant preparative methods for their synthesis. 

The UO inventors developed a selective, high yielding alternative to traditional cyclophane synthesis by the use of a pnictogen additive to direct the self-assembly of discrete disulfide cyclophanes.  Using this approach eliminates the need for caustic, temperature-sensitive methods and allows for the synthesis of formerly inaccessible, higher order species such as trimers, tetramers, pentamers, hexamers, and tetrahedra.  This method has wide functional group tolerance. This approach will be exceptionally useful in the synthetic design of many heterocycles like calixarenes, cryptands, and spherands and in ring-opening metathesis polymerization to make conjugated polymers.

The inventors are interested in finding partners who want to integrate this method in to their cyclophane synthetic process.


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For Information, Contact:
Jim Deane
University of Oregon
Darren Johnson
Mary Collins
Matthew Carnes
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